# 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_mo_dm16103_0m
_database_code_depnum_ccdc_archive 'CCDC 1499099'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2016-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl N2 O'
_chemical_formula_sum            'C16 H13 Cl N2 O'
_chemical_formula_weight         284.73
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.7439(8)
_cell_length_b                   16.180(3)
_cell_length_c                   18.262(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1401.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1697
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.8734.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11401
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.405
_diffrn_reflns_theta_min         1.682
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1714
_reflns_number_total             3171
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.2641(2) 0.53248(8) 0.14720(6) 0.0786(4) Uani 1 1 d . . . . .
O1 O 0.4093(8) 0.42571(19) 0.32840(19) 0.0928(11) Uani 1 1 d . . . . .
N1 N 0.3584(7) 0.60386(19) 0.39794(18) 0.0538(9) Uani 1 1 d . . . . .
N2 N 0.6748(8) 0.44252(19) 0.4292(2) 0.0673(10) Uani 1 1 d . . . . .
C1 C 0.3152(8) 0.6875(2) 0.3835(2) 0.0487(10) Uani 1 1 d . . . . .
C2 C 0.1216(9) 0.7298(3) 0.4275(2) 0.0585(11) Uani 1 1 d . . . . .
H2 H 0.0270 0.7020 0.4647 0.070 Uiso 1 1 calc R . . . .
C3 C 0.0714(9) 0.8122(3) 0.4159(3) 0.0641(12) Uani 1 1 d . . . . .
H3 H -0.0586 0.8402 0.4448 0.077 Uiso 1 1 calc R . . . .
C4 C 0.2148(9) 0.8535(2) 0.3609(2) 0.0662(12) Uani 1 1 d . . . . .
H4 H 0.1822 0.9096 0.3538 0.079 Uiso 1 1 calc R . . . .
C5 C 0.4033(9) 0.8134(2) 0.3169(3) 0.0632(12) Uani 1 1 d . . . . .
H5 H 0.4970 0.8423 0.2803 0.076 Uiso 1 1 calc R . . . .
C6 C 0.4565(7) 0.7288(2) 0.3268(2) 0.0474(9) Uani 1 1 d . . . . .
C7 C 0.6528(8) 0.6826(2) 0.2819(2) 0.0492(9) Uani 1 1 d . . . . .
C8 C 0.8011(9) 0.7176(3) 0.2239(2) 0.0613(11) Uani 1 1 d . . . . .
H8 H 0.7740 0.7731 0.2127 0.074 Uiso 1 1 calc R . . . .
C9 C 0.9864(8) 0.6717(3) 0.1830(2) 0.0671(12) Uani 1 1 d . . . . .
H9 H 1.0829 0.6959 0.1441 0.081 Uiso 1 1 calc R . . . .
C10 C 1.0292(8) 0.5887(3) 0.1999(2) 0.0575(11) Uani 1 1 d . . . . .
C11 C 0.8884(8) 0.5519(2) 0.2560(2) 0.0532(10) Uani 1 1 d . . . . .
H11 H 0.9201 0.4966 0.2669 0.064 Uiso 1 1 calc R . . . .
C12 C 0.6951(7) 0.5981(2) 0.2974(2) 0.0467(9) Uani 1 1 d . . . . .
C13 C 0.5359(8) 0.5629(2) 0.3569(2) 0.0494(9) Uani 1 1 d . . . . .
C14 C 0.5377(9) 0.4711(3) 0.3707(2) 0.0590(11) Uani 1 1 d . . . . .
C15 C 0.8242(10) 0.4930(3) 0.4806(3) 0.0871(16) Uani 1 1 d . . . . .
H15A H 0.8365 0.5484 0.4622 0.131 Uiso 1 1 calc GR . . . .
H15B H 1.0105 0.4712 0.4876 0.131 Uiso 1 1 calc GR . . . .
H15C H 0.7257 0.4931 0.5265 0.131 Uiso 1 1 calc GR . . . .
C16 C 0.6669(15) 0.3534(3) 0.4445(3) 0.115(2) Uani 1 1 d . . . . .
H16A H 0.7764 0.3245 0.4085 0.173 Uiso 1 1 calc GR . . . .
H16B H 0.4753 0.3344 0.4428 0.173 Uiso 1 1 calc GR . . . .
H16C H 0.7437 0.3432 0.4923 0.173 Uiso 1 1 calc GR . . . .


_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 1.731(4) . ?
O1 C14 1.228(5) . ?
N1 C1 1.394(4) . ?
N1 C13 1.308(4) . ?
N2 C14 1.332(5) . ?
N2 C15 1.432(5) . ?
N2 C16 1.469(5) . ?
C1 C2 1.399(5) . ?
C1 C6 1.403(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(5) . ?
C6 C7 1.448(5) . ?
C7 C8 1.392(5) . ?
C7 C12 1.410(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(6) . ?
C10 C11 1.360(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.404(5) . ?
C12 C13 1.440(5) . ?
C13 C14 1.506(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C1 118.6(3) . . ?
C14 N2 C15 124.7(4) . . ?
C14 N2 C16 118.8(4) . . ?
C15 N2 C16 116.5(4) . . ?
N1 C1 C2 117.6(4) . . ?
N1 C1 C6 122.1(3) . . ?
C2 C1 C6 120.4(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 118.6(3) . . ?
C5 C6 C7 123.1(4) . . ?
C8 C7 C6 123.1(4) . . ?
C8 C7 C12 118.3(4) . . ?
C12 C7 C6 118.6(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 Cl1 118.5(3) . . ?
C11 C10 Cl1 120.4(3) . . ?
C11 C10 C9 121.2(4) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C13 117.4(3) . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 C13 122.5(3) . . ?
N1 C13 C12 124.7(3) . . ?
N1 C13 C14 114.0(4) . . ?
C12 C13 C14 120.9(3) . . ?
O1 C14 N2 122.6(4) . . ?
O1 C14 C13 118.7(4) . . ?
N2 C14 C13 118.7(4) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C10 C11 C12 -178.9(3) . . . . ?
N1 C1 C2 C3 179.9(4) . . . . ?
N1 C1 C6 C5 -179.0(4) . . . . ?
N1 C1 C6 C7 0.1(5) . . . . ?
N1 C13 C14 O1 100.7(4) . . . . ?
N1 C13 C14 N2 -78.2(5) . . . . ?
C1 N1 C13 C12 0.7(5) . . . . ?
C1 N1 C13 C14 -172.4(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C1 C6 C7 C8 179.3(3) . . . . ?
C1 C6 C7 C12 -0.3(5) . . . . ?
C2 C1 C6 C5 1.6(5) . . . . ?
C2 C1 C6 C7 -179.3(3) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
C5 C6 C7 C8 -1.6(6) . . . . ?
C5 C6 C7 C12 178.7(4) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
C6 C7 C8 C9 179.6(3) . . . . ?
C6 C7 C12 C11 -178.6(3) . . . . ?
C6 C7 C12 C13 0.7(5) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C7 C12 C13 N1 -0.9(5) . . . . ?
C7 C12 C13 C14 171.7(4) . . . . ?
C8 C7 C12 C11 1.7(5) . . . . ?
C8 C7 C12 C13 -179.0(3) . . . . ?
C8 C9 C10 Cl1 180.0(3) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C7 -1.6(5) . . . . ?
C10 C11 C12 C13 179.1(3) . . . . ?
C11 C12 C13 N1 178.4(4) . . . . ?
C11 C12 C13 C14 -9.0(5) . . . . ?
C12 C7 C8 C9 -0.7(6) . . . . ?
C12 C13 C14 O1 -72.6(5) . . . . ?
C12 C13 C14 N2 108.5(4) . . . . ?
C13 N1 C1 C2 179.2(3) . . . . ?
C13 N1 C1 C6 -0.2(5) . . . . ?
C15 N2 C14 O1 -179.1(4) . . . . ?
C15 N2 C14 C13 -0.2(6) . . . . ?
C16 N2 C14 O1 -1.4(7) . . . . ?
C16 N2 C14 C13 177.5(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_20151206d_0m
_database_code_depnum_ccdc_archive 'CCDC 1499100'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl N2 O'
_chemical_formula_sum            'C18 H15 Cl N2 O'
_chemical_formula_weight         310.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   8.2579(5)
_cell_length_b                   16.2062(10)
_cell_length_c                   21.6169(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2893.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      67.75

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5795
_exptl_absorpt_correction_T_max  0.7986
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17111
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         66.00
_reflns_number_total             2509
_reflns_number_gt                2234
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'

_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)+(0.0726P)²+1.2457P] 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         2509
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02774(6) 0.14413(3) 0.404749(17) 0.03072(19) Uani 1 1 d . . .
O1 O 0.2299(2) 0.13407(10) 0.80383(6) 0.0511(5) Uani 1 1 d . . .
N1 N 0.3517(2) -0.03351(9) 0.63795(6) 0.0269(4) Uani 1 1 d . . .
N2 N 0.1865(2) 0.07424(9) 0.70984(6) 0.0314(4) Uani 1 1 d . . .
C1 C 0.4204(2) -0.09944(11) 0.60685(8) 0.0263(4) Uani 1 1 d . . .
C2 C 0.5104(3) -0.15624(12) 0.64224(9) 0.0319(5) Uani 1 1 d . . .
H2A H 0.5205 -0.1485 0.6847 0.038 Uiso 1 1 calc R . .
C3 C 0.5832(3) -0.22287(11) 0.61473(9) 0.0344(5) Uani 1 1 d . . .
H3 H 0.6442 -0.2594 0.6383 0.041 Uiso 1 1 calc R . .
C4 C 0.5653(2) -0.23560(11) 0.55111(9) 0.0327(4) Uani 1 1 d . . .
H4 H 0.6140 -0.2810 0.5325 0.039 Uiso 1 1 calc R . .
C5 C 0.4763(2) -0.18147(11) 0.51581(8) 0.0286(4) Uani 1 1 d . . .
H5 H 0.4647 -0.1910 0.4736 0.034 Uiso 1 1 calc R . .
C6 C 0.4025(2) -0.11196(10) 0.54265(7) 0.0248(4) Uani 1 1 d . . .
C7 C 0.3116(2) -0.05122(10) 0.50805(7) 0.0231(4) Uani 1 1 d . . .
C8 C 0.2883(2) -0.05573(10) 0.44339(7) 0.0259(4) Uani 1 1 d . . .
H8 H 0.3311 -0.1001 0.4216 0.031 Uiso 1 1 calc R . .
C9 C 0.2043(2) 0.00382(11) 0.41229(7) 0.0267(4) Uani 1 1 d . . .
H9 H 0.1909 0.0003 0.3696 0.032 Uiso 1 1 calc R . .
C10 C 0.1384(2) 0.07010(10) 0.44522(7) 0.0242(4) Uani 1 1 d . . .
C11 C 0.1577(2) 0.07720(10) 0.50780(7) 0.0241(4) Uani 1 1 d . . .
H11 H 0.1138 0.1221 0.5287 0.029 Uiso 1 1 calc R . .
C12 C 0.2444(2) 0.01620(10) 0.54059(7) 0.0225(4) Uani 1 1 d . . .
C13 C 0.2688(2) 0.02038(11) 0.60707(7) 0.0249(4) Uani 1 1 d . . .
C14 C 0.1982(2) 0.09195(11) 0.64390(7) 0.0285(4) Uani 1 1 d . . .
H14 H 0.0911 0.1063 0.6276 0.034 Uiso 1 1 calc R . .
C15 C 0.3098(3) 0.16882(11) 0.64245(8) 0.0326(5) Uani 1 1 d . . .
H15A H 0.4195 0.1535 0.6313 0.039 Uiso 1 1 calc R . .
H15B H 0.2703 0.2090 0.6128 0.039 Uiso 1 1 calc R . .
C16 C 0.3042(3) 0.20359(12) 0.70784(8) 0.0378(5) Uani 1 1 d . . .
H16A H 0.4117 0.2194 0.7215 0.045 Uiso 1 1 calc R . .
H16B H 0.2339 0.2515 0.7098 0.045 Uiso 1 1 calc R . .
C17 C 0.2386(3) 0.13467(12) 0.74706(8) 0.0339(5) Uani 1 1 d . . .
C18 C 0.0981(3) 0.00414(13) 0.73371(8) 0.0415(5) Uani 1 1 d . . .
H18A H 0.1618 -0.0449 0.7286 0.062 Uiso 1 1 calc R . .
H18B H -0.0020 -0.0016 0.7116 0.062 Uiso 1 1 calc R . .
H18C H 0.0759 0.0124 0.7769 0.062 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 1.7437(17) . ?
O1 C17 1.229(2) . ?
N1 C13 1.295(2) . ?
N1 C1 1.384(2) . ?
N2 C17 1.338(2) . ?
N2 C18 1.445(2) . ?
N2 C14 1.457(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.410(2) . ?
C2 C3 1.371(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(2) . ?
C7 C8 1.413(2) . ?
C7 C12 1.413(2) . ?
C8 C9 1.366(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(2) . ?
C11 C12 1.411(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.453(2) . ?
C13 C14 1.523(2) . ?
C14 C15 1.550(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.503(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C1 119.15(14) . . ?
C17 N2 C18 121.52(15) . . ?
C17 N2 C14 115.00(15) . . ?
C18 N2 C14 122.51(14) . . ?
N1 C1 C2 117.19(15) . . ?
N1 C1 C6 123.09(16) . . ?
C2 C1 C6 119.72(17) . . ?
C3 C2 C1 120.67(18) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.76(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.52(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.90(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.42(16) . . ?
C5 C6 C7 123.84(15) . . ?
C1 C6 C7 117.73(15) . . ?
C8 C7 C12 118.63(15) . . ?
C8 C7 C6 123.15(15) . . ?
C12 C7 C6 118.21(14) . . ?
C9 C8 C7 121.30(15) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.31(14) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 121.55(15) . . ?
C11 C10 Cl1 119.97(13) . . ?
C9 C10 Cl1 118.47(12) . . ?
C10 C11 C12 119.81(15) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 119.39(14) . . ?
C11 C12 C13 122.31(15) . . ?
C7 C12 C13 118.29(15) . . ?
N1 C13 C12 123.50(16) . . ?
N1 C13 C14 116.52(14) . . ?
C12 C13 C14 119.97(15) . . ?
N2 C14 C13 112.77(14) . . ?
N2 C14 C15 102.57(13) . . ?
C13 C14 C15 111.96(15) . . ?
N2 C14 H14 109.8 . . ?
C13 C14 H14 109.8 . . ?
C15 C14 H14 109.8 . . ?
C16 C15 C14 105.12(14) . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C17 C16 C15 105.04(15) . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
O1 C17 N2 125.14(18) . . ?
O1 C17 C16 126.14(17) . . ?
N2 C17 C16 108.69(15) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C2 179.61(17) . . . . ?
C13 N1 C1 C6 -1.1(3) . . . . ?
N1 C1 C2 C3 -179.54(18) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 178.00(17) . . . . ?
N1 C1 C6 C5 -179.40(17) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C7 1.8(3) . . . . ?
C2 C1 C6 C7 -178.91(17) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C1 C6 C7 C8 178.48(16) . . . . ?
C5 C6 C7 C12 -179.58(16) . . . . ?
C1 C6 C7 C12 -0.9(2) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C6 C7 C8 C9 -178.69(16) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 Cl1 -178.58(14) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
Cl1 C10 C11 C12 178.63(13) . . . . ?
C10 C11 C12 C7 0.6(3) . . . . ?
C10 C11 C12 C13 -179.99(16) . . . . ?
C8 C7 C12 C11 -0.6(2) . . . . ?
C6 C7 C12 C11 178.80(15) . . . . ?
C8 C7 C12 C13 179.98(16) . . . . ?
C6 C7 C12 C13 -0.6(2) . . . . ?
C1 N1 C13 C12 -0.6(3) . . . . ?
C1 N1 C13 C14 -179.27(16) . . . . ?
C11 C12 C13 N1 -177.98(17) . . . . ?
C7 C12 C13 N1 1.5(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C7 C12 C13 C14 -179.91(16) . . . . ?
C17 N2 C14 C13 134.43(18) . . . . ?
C18 N2 C14 C13 -56.7(2) . . . . ?
C17 N2 C14 C15 13.8(2) . . . . ?
C18 N2 C14 C15 -177.33(18) . . . . ?
N1 C13 C14 N2 -20.1(2) . . . . ?
C12 C13 C14 N2 161.14(16) . . . . ?
N1 C13 C14 C15 94.94(18) . . . . ?
C12 C13 C14 C15 -83.8(2) . . . . ?
N2 C14 C15 C16 -18.39(19) . . . . ?
C13 C14 C15 C16 -139.55(16) . . . . ?
C14 C15 C16 C17 17.2(2) . . . . ?
C18 N2 C17 O1 6.4(3) . . . . ?
C14 N2 C17 O1 175.3(2) . . . . ?
C18 N2 C17 C16 -172.04(18) . . . . ?
C14 N2 C17 C16 -3.1(2) . . . . ?
C15 C16 C17 O1 172.2(2) . . . . ?
C15 C16 C17 N2 -9.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        66.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.086
