# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_is_ac13
_database_code_depnum_ccdc_archive 'CCDC 1410098'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
7-chloro-4-(4-methoxyphenyl)-1-methylindoline-2,3-dione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl N O3'
_chemical_formula_sum            'C16 H12 Cl N O3'
_chemical_formula_weight         301.72

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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'

_cell_length_a                   7.3328(3)
_cell_length_b                   9.2003(4)
_cell_length_c                   19.7779(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1334.30(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7138
_cell_measurement_theta_min      4.883
_cell_measurement_theta_max      61.636

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9165
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_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            23516
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         32.50
_reflns_number_total             4706
_reflns_number_gt                4030
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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)+(0.0392P)²+0.2301P] 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   0.05(5)
_refine_ls_number_reflns         4706
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.58278(5) 0.43247(4) -0.233486(17) 0.02908(9) Uani 1 1 d . . .
N1 N 0.39662(16) 0.31926(13) -0.09327(6) 0.0197(2) Uani 1 1 d . . .
O1 O 0.24412(16) 0.19788(12) -0.00819(6) 0.0272(2) Uani 1 1 d . . .
O2 O 0.33720(15) 0.45543(12) 0.06901(5) 0.0256(2) Uani 1 1 d . . .
O3 O 0.56723(16) 1.01524(13) 0.20488(5) 0.0303(2) Uani 1 1 d . . .
C1 C 0.55179(17) 0.52304(16) -0.15684(6) 0.0192(3) Uani 1 1 d . . .
C2 C 0.60876(18) 0.66701(16) -0.15288(7) 0.0205(3) Uani 1 1 d . . .
H2 H 0.6580 0.7127 -0.1919 0.025 Uiso 1 1 calc R . .
C3 C 0.59526(19) 0.74468(16) -0.09355(7) 0.0200(3) Uani 1 1 d . . .
H3 H 0.6319 0.8437 -0.0928 0.024 Uiso 1 1 calc R . .
C4 C 0.52843(17) 0.68038(15) -0.03417(7) 0.0175(2) Uani 1 1 d . . .
C5 C 0.46733(17) 0.53698(14) -0.03906(6) 0.0162(2) Uani 1 1 d . . .
C6 C 0.37603(17) 0.44099(15) 0.01007(6) 0.0186(2) Uani 1 1 d . . .
C7 C 0.32813(18) 0.30172(15) -0.02971(7) 0.0196(3) Uani 1 1 d . . .
C8 C 0.47587(17) 0.45794(15) -0.10043(6) 0.0171(2) Uani 1 1 d . . .
C9 C 0.3792(3) 0.20564(18) -0.14363(8) 0.0372(4) Uani 1 1 d . . .
H9A H 0.3117 0.1235 -0.1244 0.056 Uiso 1 1 calc R . .
H9B H 0.5008 0.1731 -0.1576 0.056 Uiso 1 1 calc R . .
H9C H 0.3133 0.2434 -0.1830 0.056 Uiso 1 1 calc R . .
C10 C 0.53273(18) 0.76353(15) 0.02995(7) 0.0182(2) Uani 1 1 d . . .
C11 C 0.48300(17) 0.91084(15) 0.03123(7) 0.0188(3) Uani 1 1 d . . .
H11 H 0.4406 0.9558 -0.0091 0.023 Uiso 1 1 calc R . .
C12 C 0.49447(18) 0.99186(16) 0.09005(7) 0.0208(3) Uani 1 1 d . . .
H12 H 0.4592 1.0912 0.0901 0.025 Uiso 1 1 calc R . .
C13 C 0.55826(17) 0.92652(17) 0.14935(7) 0.0215(3) Uani 1 1 d . . .
C14 C 0.60875(19) 0.78115(16) 0.14913(7) 0.0221(3) Uani 1 1 d . . .
H14 H 0.6521 0.7366 0.1894 0.026 Uiso 1 1 calc R . .
C15 C 0.59564(18) 0.70112(16) 0.08978(7) 0.0207(3) Uani 1 1 d . . .
H15 H 0.6303 0.6016 0.0900 0.025 Uiso 1 1 calc R . .
C16 C 0.6105(2) 0.9489(2) 0.26805(7) 0.0356(4) Uani 1 1 d . . .
H16A H 0.5227 0.8712 0.2775 0.053 Uiso 1 1 calc R . .
H16B H 0.6048 1.0220 0.3040 0.053 Uiso 1 1 calc R . .
H16C H 0.7337 0.9080 0.2660 0.053 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.7447(14) . ?
N1 C7 1.3631(17) . ?
N1 C8 1.4092(18) . ?
N1 C9 1.4496(19) . ?
O1 C7 1.2138(17) . ?
O2 C6 1.2073(15) . ?
O3 C13 1.3700(17) . ?
O3 C16 1.4262(19) . ?
C1 C8 1.3833(18) . ?
C1 C2 1.391(2) . ?
C2 C3 1.3775(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4034(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3967(19) . ?
C4 C10 1.4812(19) . ?
C5 C8 1.4163(17) . ?
C5 C6 1.4738(18) . ?
C6 C7 1.544(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.3939(18) . ?
C10 C11 1.404(2) . ?
C11 C12 1.3842(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3984(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C14 C15 1.3889(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 110.60(11) . . ?
C7 N1 C9 121.05(12) . . ?
C8 N1 C9 128.33(12) . . ?
C13 O3 C16 117.26(12) . . ?
C8 C1 C2 119.19(12) . . ?
C8 C1 Cl1 123.12(11) . . ?
C2 C1 Cl1 117.68(10) . . ?
C3 C2 C1 121.35(12) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.29(13) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 116.89(12) . . ?
C5 C4 C10 123.64(12) . . ?
C3 C4 C10 119.42(12) . . ?
C4 C5 C8 122.02(12) . . ?
C4 C5 C6 131.76(12) . . ?
C8 C5 C6 106.10(11) . . ?
O2 C6 C5 132.67(13) . . ?
O2 C6 C7 121.98(12) . . ?
C5 C6 C7 105.35(10) . . ?
O1 C7 N1 127.12(14) . . ?
O1 C7 C6 126.15(13) . . ?
N1 C7 C6 106.73(11) . . ?
C1 C8 N1 129.72(12) . . ?
C1 C8 C5 119.12(12) . . ?
N1 C8 C5 111.13(11) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 117.92(12) . . ?
C15 C10 C4 121.41(12) . . ?
C11 C10 C4 120.57(12) . . ?
C12 C11 C10 121.29(13) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.58(14) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O3 C13 C14 124.33(13) . . ?
O3 C13 C12 115.61(13) . . ?
C14 C13 C12 120.06(13) . . ?
C13 C14 C15 119.67(13) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C10 121.47(13) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 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
C8 C1 C2 C3 1.6(2) . . . . ?
Cl1 C1 C2 C3 -177.64(11) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 -3.38(19) . . . . ?
C2 C3 C4 C10 174.19(12) . . . . ?
C3 C4 C5 C8 1.50(18) . . . . ?
C10 C4 C5 C8 -175.97(11) . . . . ?
C3 C4 C5 C6 -174.07(13) . . . . ?
C10 C4 C5 C6 8.5(2) . . . . ?
C4 C5 C6 O2 -4.7(2) . . . . ?
C8 C5 C6 O2 179.17(14) . . . . ?
C4 C5 C6 C7 174.40(13) . . . . ?
C8 C5 C6 C7 -1.69(13) . . . . ?
C8 N1 C7 O1 176.34(14) . . . . ?
C9 N1 C7 O1 -2.2(2) . . . . ?
C8 N1 C7 C6 -3.04(14) . . . . ?
C9 N1 C7 C6 178.45(13) . . . . ?
O2 C6 C7 O1 2.8(2) . . . . ?
C5 C6 C7 O1 -176.47(14) . . . . ?
O2 C6 C7 N1 -177.83(12) . . . . ?
C5 C6 C7 N1 2.91(14) . . . . ?
C2 C1 C8 N1 174.75(13) . . . . ?
Cl1 C1 C8 N1 -6.0(2) . . . . ?
C2 C1 C8 C5 -3.45(18) . . . . ?
Cl1 C1 C8 C5 175.78(9) . . . . ?
C7 N1 C8 C1 -176.25(13) . . . . ?
C9 N1 C8 C1 2.1(2) . . . . ?
C7 N1 C8 C5 2.06(15) . . . . ?
C9 N1 C8 C5 -179.55(15) . . . . ?
C4 C5 C8 C1 1.90(18) . . . . ?
C6 C5 C8 C1 178.46(11) . . . . ?
C4 C5 C8 N1 -176.61(11) . . . . ?
C6 C5 C8 N1 -0.06(14) . . . . ?
C5 C4 C10 C15 43.81(19) . . . . ?
C3 C4 C10 C15 -133.59(14) . . . . ?
C5 C4 C10 C11 -139.88(13) . . . . ?
C3 C4 C10 C11 42.72(18) . . . . ?
C15 C10 C11 C12 -0.48(19) . . . . ?
C4 C10 C11 C12 -176.92(12) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C16 O3 C13 C14 -7.8(2) . . . . ?
C16 O3 C13 C12 172.66(13) . . . . ?
C11 C12 C13 O3 179.21(12) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
O3 C13 C14 C15 -179.47(13) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
C4 C10 C15 C14 176.57(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        32.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_is_ac8
_database_code_depnum_ccdc_archive 'CCDC 1410099'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
7-chloro-1-methyl-4-(4-tolyl)indoline-2,3-dione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl N O2'
_chemical_formula_sum            'C16 H12 Cl N O2'
_chemical_formula_weight         285.72

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   3.8951(6)
_cell_length_b                   24.185(3)
_cell_length_c                   13.5874(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.733(7)
_cell_angle_gamma                90.00
_cell_volume                     1277.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    381
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      17.93

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7563
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_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            2893
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1668
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2894
_reflns_number_gt                1539
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex v7.51a'
_computing_cell_refinement       'Bruker Apex v7.51a'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 The crystal was a partial merohedral twin (1 0 0  0 -1 0  -0.5 0 -1).
 The structure was refined with HKLF5 data including both twin components 
 (0.776/0.224).

 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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)+(0.0439P)²+0.6173P] 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         2894
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.0436(3) 0.42332(4) 0.42040(8) 0.0328(3) Uani 1 1 d . . .
N1 N 0.4998(8) 0.39146(11) 0.6221(2) 0.0238(8) Uani 1 1 d . . .
O1 O 0.8502(7) 0.38908(10) 0.7662(2) 0.0356(8) Uani 1 1 d . . .
O2 O 0.8421(7) 0.27106(10) 0.7278(2) 0.0327(7) Uani 1 1 d . . .
C1 C 0.6973(11) 0.36678(15) 0.6966(3) 0.0258(10) Uani 1 1 d . . .
C2 C 0.6896(10) 0.30412(15) 0.6746(3) 0.0240(9) Uani 1 1 d . . .
C3 C 0.4804(10) 0.29804(14) 0.5818(3) 0.0201(9) Uani 1 1 d . . .
C4 C 0.3748(10) 0.35199(13) 0.5513(3) 0.0200(9) Uani 1 1 d . . .
C5 C 0.4302(10) 0.45079(14) 0.6242(3) 0.0310(11) Uani 1 1 d . . .
H5A H 0.5427 0.4669 0.6841 0.047 Uiso 1 1 calc R . .
H5B H 0.1814 0.4569 0.6237 0.047 Uiso 1 1 calc R . .
H5C H 0.5199 0.4683 0.5661 0.047 Uiso 1 1 calc R . .
C6 C 0.4017(10) 0.25148(14) 0.5221(3) 0.0205(9) Uani 1 1 d . . .
C7 C 0.2263(10) 0.26144(14) 0.4313(3) 0.0258(10) Uani 1 1 d . . .
H7 H 0.1785 0.2313 0.3877 0.031 Uiso 1 1 calc R . .
C8 C 0.1200(10) 0.31362(14) 0.4031(3) 0.0226(9) Uani 1 1 d . . .
H8 H -0.0049 0.3185 0.3413 0.027 Uiso 1 1 calc R . .
C9 C 0.1914(10) 0.35943(14) 0.4630(3) 0.0230(9) Uani 1 1 d . . .
C10 C 0.4979(9) 0.19435(14) 0.5527(3) 0.0200(9) Uani 1 1 d . . .
C11 C 0.4472(10) 0.17464(14) 0.6469(3) 0.0243(10) Uani 1 1 d . . .
H11 H 0.3541 0.1983 0.6943 0.029 Uiso 1 1 calc R . .
C12 C 0.5322(10) 0.12084(15) 0.6714(3) 0.0263(10) Uani 1 1 d . . .
H12 H 0.4959 0.1078 0.7359 0.032 Uiso 1 1 calc R . .
C13 C 0.6706(10) 0.08506(14) 0.6035(3) 0.0266(10) Uani 1 1 d . . .
C14 C 0.7148(10) 0.10513(15) 0.5103(3) 0.0289(11) Uani 1 1 d . . .
H14 H 0.8084 0.0816 0.4629 0.035 Uiso 1 1 calc R . .
C15 C 0.6262(10) 0.15868(14) 0.4842(3) 0.0242(10) Uani 1 1 d . . .
H15 H 0.6533 0.1712 0.4189 0.029 Uiso 1 1 calc R . .
C16 C 0.7717(11) 0.02655(15) 0.6330(3) 0.0394(12) Uani 1 1 d . . .
H16A H 0.5642 0.0039 0.6361 0.059 Uiso 1 1 calc R . .
H16B H 0.8976 0.0270 0.6978 0.059 Uiso 1 1 calc R . .
H16C H 0.9186 0.0110 0.5841 0.059 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.735(4) . ?
N1 C1 1.368(5) . ?
N1 C4 1.418(4) . ?
N1 C5 1.461(4) . ?
O1 C1 1.211(4) . ?
O2 C2 1.208(4) . ?
C1 C2 1.544(5) . ?
C2 C3 1.464(5) . ?
C3 C6 1.409(5) . ?
C3 C4 1.421(5) . ?
C4 C9 1.368(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.391(5) . ?
C6 C10 1.484(5) . ?
C7 C8 1.375(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C10 C15 1.386(5) . ?
C10 C11 1.392(5) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(5) . ?
C13 C16 1.516(5) . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 111.1(3) . . ?
C1 N1 C5 120.7(3) . . ?
C4 N1 C5 128.2(3) . . ?
O1 C1 N1 127.4(3) . . ?
O1 C1 C2 126.2(4) . . ?
N1 C1 C2 106.4(3) . . ?
O2 C2 C3 132.3(4) . . ?
O2 C2 C1 122.1(4) . . ?
C3 C2 C1 105.5(3) . . ?
C6 C3 C4 121.2(4) . . ?
C6 C3 C2 131.6(3) . . ?
C4 C3 C2 107.0(3) . . ?
C9 C4 N1 130.0(3) . . ?
C9 C4 C3 120.0(3) . . ?
N1 C4 C3 109.9(3) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C3 116.6(3) . . ?
C7 C6 C10 120.7(3) . . ?
C3 C6 C10 122.8(3) . . ?
C8 C7 C6 121.9(4) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 121.5(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 118.8(3) . . ?
C4 C9 Cl1 123.5(3) . . ?
C8 C9 Cl1 117.7(3) . . ?
C15 C10 C11 118.9(3) . . ?
C15 C10 C6 119.1(3) . . ?
C11 C10 C6 121.9(3) . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.7(3) . . ?
C14 C13 C16 121.7(4) . . ?
C12 C13 C16 120.5(4) . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 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
C4 N1 C1 O1 177.3(4) . . . . ?
C5 N1 C1 O1 -5.0(6) . . . . ?
C4 N1 C1 C2 -2.4(4) . . . . ?
C5 N1 C1 C2 175.3(3) . . . . ?
O1 C1 C2 O2 0.2(7) . . . . ?
N1 C1 C2 O2 180.0(4) . . . . ?
O1 C1 C2 C3 -178.4(4) . . . . ?
N1 C1 C2 C3 1.4(4) . . . . ?
O2 C2 C3 C6 -3.2(8) . . . . ?
C1 C2 C3 C6 175.2(4) . . . . ?
O2 C2 C3 C4 -178.2(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 N1 C4 C9 -174.7(4) . . . . ?
C5 N1 C4 C9 7.8(7) . . . . ?
C1 N1 C4 C3 2.7(4) . . . . ?
C5 N1 C4 C3 -174.8(3) . . . . ?
C6 C3 C4 C9 0.4(6) . . . . ?
C2 C3 C4 C9 176.0(4) . . . . ?
C6 C3 C4 N1 -177.3(3) . . . . ?
C2 C3 C4 N1 -1.6(4) . . . . ?
C4 C3 C6 C7 1.9(5) . . . . ?
C2 C3 C6 C7 -172.4(4) . . . . ?
C4 C3 C6 C10 -178.0(3) . . . . ?
C2 C3 C6 C10 7.6(6) . . . . ?
C3 C6 C7 C8 -3.0(6) . . . . ?
C10 C6 C7 C8 176.9(4) . . . . ?
C6 C7 C8 C9 1.8(6) . . . . ?
N1 C4 C9 C8 175.4(4) . . . . ?
C3 C4 C9 C8 -1.8(6) . . . . ?
N1 C4 C9 Cl1 -4.2(6) . . . . ?
C3 C4 C9 Cl1 178.7(3) . . . . ?
C7 C8 C9 C4 0.7(6) . . . . ?
C7 C8 C9 Cl1 -179.7(3) . . . . ?
C7 C6 C10 C15 42.0(5) . . . . ?
C3 C6 C10 C15 -138.0(4) . . . . ?
C7 C6 C10 C11 -134.7(4) . . . . ?
C3 C6 C10 C11 45.3(5) . . . . ?
C15 C10 C11 C12 1.6(6) . . . . ?
C6 C10 C11 C12 178.3(3) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C11 C12 C13 C16 178.2(4) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C16 C13 C14 C15 -179.2(4) . . . . ?
C13 C14 C15 C10 1.8(6) . . . . ?
C11 C10 C15 C14 -2.5(6) . . . . ?
C6 C10 C15 C14 -179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.089

#=====================  End of is_ac8 =================================

#=====================  End of CIF submission =================================
