# Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is (c) The Owner Societies 2010


data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)
_journal_coden_cambridge         1326
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Jonathan Clayden'
_publ_contact_author_email       j.p.clayden@manchester.ac.uk
_publ_author_name                I.H.Hillier

data_s2742bm
_database_code_depnum_ccdc_archive 'CCDC 768560'
#TrackingRef 's2742bm.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
#------------------------------------------------------------------------------
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl N2 O'
_chemical_formula_weight         330.84

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   8.9347(16)
_cell_length_b                   12.250(2)
_cell_length_c                   16.332(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1787.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    773
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      22.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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            9355
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3151
_reflns_number_gt                2788
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0418P)^2^+0.1070P] where P=(Fo^2^+2Fc^2^)/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   0.60(7)
_refine_ls_number_reflns         3151
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 1.22850(7) 0.97909(6) 0.48072(5) 0.0525(2) Uani 1 1 d . . .
O1 O 0.50948(18) 0.73089(17) 0.67829(11) 0.0501(5) Uani 1 1 d . . .
N1 N 0.6747(2) 0.87209(16) 0.66356(13) 0.0401(5) Uani 1 1 d . . .
N2 N 0.7467(2) 0.70704(14) 0.72266(11) 0.0282(4) Uani 1 1 d . . .
C1 C 0.8111(3) 0.89561(17) 0.62094(13) 0.0288(5) Uani 1 1 d . . .
C2 C 0.8942(3) 0.98657(19) 0.64229(14) 0.0396(6) Uani 1 1 d . . .
H2 H 0.8630 1.0315 0.6865 0.048 Uiso 1 1 calc R . .
C3 C 1.0222(3) 1.01181(19) 0.59940(15) 0.0403(6) Uani 1 1 d . . .
H3 H 1.0799 1.0740 0.6140 0.048 Uiso 1 1 calc R . .
C4 C 1.0659(3) 0.94644(19) 0.53529(15) 0.0325(6) Uani 1 1 d . . .
C5 C 0.9840(2) 0.85712(17) 0.51207(15) 0.0298(5) Uani 1 1 d . . .
H5 H 1.0152 0.8130 0.4674 0.036 Uiso 1 1 calc R . .
C6 C 0.8549(2) 0.83257(18) 0.55506(13) 0.0269(5) Uani 1 1 d . . .
H6 H 0.7958 0.7717 0.5391 0.032 Uiso 1 1 calc R . .
C7 C 0.5480(3) 0.9403(3) 0.6379(2) 0.0753(11) Uani 1 1 d . . .
H7A H 0.5252 0.9260 0.5802 0.113 Uiso 1 1 calc R . .
H7B H 0.5739 1.0175 0.6449 0.113 Uiso 1 1 calc R . .
H7C H 0.4602 0.9229 0.6715 0.113 Uiso 1 1 calc R . .
C8 C 0.6373(3) 0.7661(2) 0.68670(14) 0.0329(6) Uani 1 1 d . . .
C9 C 0.7187(3) 0.59094(19) 0.73641(17) 0.0475(7) Uani 1 1 d . . .
H9A H 0.6931 0.5790 0.7941 0.071 Uiso 1 1 calc R . .
H9B H 0.8087 0.5491 0.7226 0.071 Uiso 1 1 calc R . .
H9C H 0.6354 0.5670 0.7017 0.071 Uiso 1 1 calc R . .
C10 C 0.8859(2) 0.74776(16) 0.75492(13) 0.0220(5) Uani 1 1 d . . .
C11 C 0.8982(3) 0.80821(16) 0.82753(13) 0.0269(5) Uani 1 1 d . . .
C12 C 1.0443(3) 0.83715(18) 0.84925(15) 0.0364(6) Uani 1 1 d . . .
H12 H 1.0580 0.8793 0.8975 0.044 Uiso 1 1 calc R . .
C13 C 1.1691(3) 0.8086(2) 0.80533(16) 0.0401(6) Uani 1 1 d . . .
H13 H 1.2653 0.8313 0.8232 0.048 Uiso 1 1 calc R . .
C14 C 1.1545(3) 0.74674(18) 0.73488(15) 0.0342(6) Uani 1 1 d . . .
H14 H 1.2399 0.7254 0.7042 0.041 Uiso 1 1 calc R . .
C15 C 1.0133(2) 0.71721(17) 0.71076(13) 0.0268(5) Uani 1 1 d . . .
H15 H 1.0016 0.6747 0.6626 0.032 Uiso 1 1 calc R . .
C16 C 0.7719(3) 0.84642(18) 0.88581(14) 0.0382(6) Uani 1 1 d . . .
C17 C 0.7594(5) 0.9699(2) 0.8772(2) 0.1128(18) Uani 1 1 d . . .
H17A H 0.6983 0.9990 0.9220 0.169 Uiso 1 1 calc R . .
H17B H 0.7122 0.9877 0.8247 0.169 Uiso 1 1 calc R . .
H17C H 0.8595 1.0024 0.8793 0.169 Uiso 1 1 calc R . .
C18 C 0.8138(4) 0.8202(3) 0.97422(17) 0.0649(9) Uani 1 1 d . . .
H18A H 0.7365 0.8487 1.0111 0.097 Uiso 1 1 calc R . .
H18B H 0.9102 0.8542 0.9874 0.097 Uiso 1 1 calc R . .
H18C H 0.8216 0.7409 0.9810 0.097 Uiso 1 1 calc R . .
C19 C 0.6210(3) 0.7936(4) 0.8743(2) 0.0902(14) Uani 1 1 d . . .
H19A H 0.6315 0.7141 0.8778 0.135 Uiso 1 1 calc R . .
H19B H 0.5807 0.8135 0.8205 0.135 Uiso 1 1 calc R . .
H19C H 0.5526 0.8189 0.9172 0.135 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0338(4) 0.0599(4) 0.0637(4) 0.0222(4) 0.0037(3) -0.0136(3)
O1 0.0215(10) 0.0870(14) 0.0419(10) -0.0027(10) -0.0018(8) -0.0067(9)
N1 0.0290(11) 0.0497(13) 0.0416(12) 0.0063(10) 0.0104(10) 0.0195(10)
N2 0.0235(11) 0.0309(9) 0.0301(10) -0.0004(8) -0.0006(8) -0.0065(9)
C1 0.0306(14) 0.0282(12) 0.0277(12) 0.0037(10) 0.0021(10) 0.0131(10)
C2 0.0616(17) 0.0273(12) 0.0300(13) 0.0001(11) 0.0026(12) 0.0098(12)
C3 0.0584(17) 0.0244(12) 0.0382(14) 0.0061(11) -0.0130(13) -0.0080(12)
C4 0.0303(13) 0.0348(13) 0.0323(14) 0.0114(11) -0.0033(11) -0.0040(10)
C5 0.0313(13) 0.0300(12) 0.0279(12) 0.0008(10) 0.0014(11) 0.0050(10)
C6 0.0240(12) 0.0263(11) 0.0306(12) 0.0001(9) -0.0013(10) -0.0009(9)
C7 0.0482(19) 0.093(2) 0.085(3) 0.031(2) 0.0220(18) 0.0443(18)
C8 0.0219(14) 0.0498(15) 0.0271(12) -0.0009(11) 0.0055(10) 0.0042(11)
C9 0.0481(17) 0.0404(14) 0.0539(16) 0.0063(13) -0.0083(14) -0.0211(13)
C10 0.0220(11) 0.0180(10) 0.0261(11) 0.0036(10) 0.0007(9) -0.0023(9)
C11 0.0318(13) 0.0219(11) 0.0269(12) 0.0059(10) 0.0006(10) -0.0010(9)
C12 0.0418(15) 0.0308(13) 0.0366(14) -0.0018(11) -0.0107(12) -0.0107(11)
C13 0.0267(14) 0.0410(14) 0.0526(17) 0.0132(13) -0.0092(12) -0.0146(11)
C14 0.0211(13) 0.0353(13) 0.0461(15) 0.0141(12) 0.0048(11) 0.0055(10)
C15 0.0280(13) 0.0221(11) 0.0303(12) 0.0038(9) 0.0032(10) 0.0015(9)
C16 0.0477(16) 0.0372(13) 0.0296(13) -0.0006(11) 0.0108(12) 0.0061(12)
C17 0.173(4) 0.0512(19) 0.114(3) 0.028(2) 0.099(3) 0.054(3)
C18 0.076(2) 0.088(2) 0.0307(15) -0.0106(16) 0.0096(16) -0.0059(18)
C19 0.0331(18) 0.194(4) 0.0438(18) -0.031(2) 0.0230(15) -0.004(2)

_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 C4 1.750(2) . ?
O1 C8 1.229(3) . ?
N1 C8 1.393(3) . ?
N1 C1 1.432(3) . ?
N1 C7 1.468(3) . ?
N2 C8 1.350(3) . ?
N2 C10 1.440(3) . ?
N2 C9 1.461(3) . ?
C1 C6 1.381(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.399(3) . ?
C10 C11 1.402(3) . ?
C11 C12 1.398(3) . ?
C11 C16 1.549(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C19 1.508(4) . ?
C16 C17 1.523(4) . ?
C16 C18 1.526(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C8 N1 C1 121.54(18) . . ?
C8 N1 C7 115.0(2) . . ?
C1 N1 C7 113.8(2) . . ?
C8 N2 C10 126.78(18) . . ?
C8 N2 C9 117.6(2) . . ?
C10 N2 C9 115.41(18) . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 N1 120.5(2) . . ?
C2 C1 N1 119.7(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 Cl1 119.00(19) . . ?
C3 C4 Cl1 119.38(18) . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N2 122.2(2) . . ?
O1 C8 N1 121.3(2) . . ?
N2 C8 N1 116.4(2) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.9(2) . . ?
C15 C10 N2 114.94(18) . . ?
C11 C10 N2 124.06(19) . . ?
C12 C11 C10 114.9(2) . . ?
C12 C11 C16 116.6(2) . . ?
C10 C11 C16 128.5(2) . . ?
C13 C12 C11 124.2(2) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
C19 C16 C17 110.4(3) . . ?
C19 C16 C18 104.3(2) . . ?
C17 C16 C18 108.3(3) . . ?
C19 C16 C11 116.5(2) . . ?
C17 C16 C11 107.3(2) . . ?
C18 C16 C11 109.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 N1 C1 C6 46.3(3) . . . . ?
C7 N1 C1 C6 -98.0(3) . . . . ?
C8 N1 C1 C2 -138.2(2) . . . . ?
C7 N1 C1 C2 77.5(3) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
N1 C1 C2 C3 -177.5(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 Cl1 179.82(18) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
Cl1 C4 C5 C6 -179.36(16) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
N1 C1 C6 C5 177.91(19) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C10 N2 C8 O1 -162.5(2) . . . . ?
C9 N2 C8 O1 12.5(3) . . . . ?
C10 N2 C8 N1 14.0(3) . . . . ?
C9 N2 C8 N1 -171.0(2) . . . . ?
C1 N1 C8 O1 -137.3(2) . . . . ?
C7 N1 C8 O1 6.6(3) . . . . ?
C1 N1 C8 N2 46.2(3) . . . . ?
C7 N1 C8 N2 -169.9(2) . . . . ?
C8 N2 C10 C15 -110.6(2) . . . . ?
C9 N2 C10 C15 74.2(2) . . . . ?
C8 N2 C10 C11 73.0(3) . . . . ?
C9 N2 C10 C11 -102.1(2) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
N2 C10 C11 C12 178.17(19) . . . . ?
C15 C10 C11 C16 -178.01(19) . . . . ?
N2 C10 C11 C16 -1.9(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C16 C11 C12 C13 178.9(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 -1.6(3) . . . . ?
N2 C10 C15 C14 -178.09(19) . . . . ?
C12 C11 C16 C19 -165.8(3) . . . . ?
C10 C11 C16 C19 14.2(4) . . . . ?
C12 C11 C16 C17 70.0(3) . . . . ?
C10 C11 C16 C17 -110.0(3) . . . . ?
C12 C11 C16 C18 -47.6(3) . . . . ?
C10 C11 C16 C18 132.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.036