# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Masami Sakamoto'
_publ_contact_author_address     
;
Department of Applied Chemistry and Biotechnology
Chiba University, Graduate School of Engineering
Yayoi-cho
Inage-ku
Chiba
263-8522
JAPAN
;

_publ_contact_author_email       SAKAMOTOM@FACULTY.CHIBA-U.JP

_publ_section_title              
;
Asymmetric SNAr Reaction Using the Molecular Chirality
in Crystal
;
loop_
_publ_author_name
'Masami Sakamoto'
'Kazuyuki Fujita'
'Tsutomu Fujita'
'Shuichiro Kobaru'
'Takashi Mino'
'Atsushi Unosawa'

data_saka48_p212121
_database_code_depnum_ccdc_archive 'CCDC 638448'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C16 H17 N O2'

_chemical_formula_weight         255.31

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source

C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   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                   7.6281(15)

_cell_length_b                   11.856(2)

_cell_length_c                   14.408(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1303.0(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    173

_cell_measurement_reflns_used    5192

_cell_measurement_theta_min      2.22

_cell_measurement_theta_max      28.15

_exptl_crystal_description       prismatic

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.50

_exptl_crystal_size_mid          0.40

_exptl_crystal_size_min          0.40

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.301

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    0.086

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.9584

_exptl_absorpt_correction_T_max  0.9665

_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      173

_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  'APEX II CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_standards_number         0

_diffrn_standards_interval_count .

_diffrn_standards_interval_time  .

_diffrn_standards_decay_%        0

_diffrn_reflns_number            7321

_diffrn_reflns_av_R_equivalents  0.0188

_diffrn_reflns_av_sigmaI/netI    0.0206

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       4

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         2.22

_diffrn_reflns_theta_max         28.30

_reflns_number_total             2991

_reflns_number_gt                2880

_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^)+(0.1000P)^2^+0.2395P] 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   -1.0(10)

_refine_ls_number_reflns         2991

_refine_ls_number_parameters     173

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0351

_refine_ls_R_factor_gt           0.0339

_refine_ls_wR_factor_ref         0.0955

_refine_ls_wR_factor_gt          0.0937

_refine_ls_goodness_of_fit_ref   0.735

_refine_ls_restrained_S_all      0.735

_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

C1 C 0.24084(13) 0.74311(8) 0.75396(7) 0.0190(2) Uani 1 1 d . . .
C2 C 0.19438(14) 0.63308(9) 0.77355(7) 0.0212(2) Uani 1 1 d . . .
C3 C 0.10072(15) 0.56743(9) 0.70803(8) 0.0239(2) Uani 1 1 d . . .
H3 H 0.0661 0.4927 0.7231 0.029 Uiso 1 1 calc R . .
C4 C 0.06042(15) 0.61178(9) 0.62338(8) 0.0244(2) Uani 1 1 d . . .
H4 H -0.0031 0.5673 0.5801 0.029 Uiso 1 1 calc R . .
C5 C 0.11131(14) 0.72285(9) 0.59855(7) 0.0217(2) Uani 1 1 d . . .
C6 C 0.07748(16) 0.76863(10) 0.50916(8) 0.0269(2) Uani 1 1 d . . .
H6 H 0.0159 0.7248 0.4646 0.032 Uiso 1 1 calc R . .
C7 C 0.13237(17) 0.87511(11) 0.48631(8) 0.0285(3) Uani 1 1 d . . .
H7 H 0.1115 0.9039 0.4258 0.034 Uiso 1 1 calc R . .
C8 C 0.22006(16) 0.94210(9) 0.55294(8) 0.0270(2) Uani 1 1 d . . .
H8 H 0.2574 1.0160 0.5369 0.032 Uiso 1 1 calc R . .
C9 C 0.25182(14) 0.90162(9) 0.64053(8) 0.0234(2) Uani 1 1 d . . .
H9 H 0.3082 0.9485 0.6849 0.028 Uiso 1 1 calc R . .
C10 C 0.20113(13) 0.79004(8) 0.66558(7) 0.0193(2) Uani 1 1 d . . .
C11 C 0.32571(14) 0.81678(9) 0.82644(7) 0.0202(2) Uani 1 1 d . . .
C12 C 0.24130(18) 0.47553(10) 0.87469(9) 0.0318(3) Uani 1 1 d . . .
H12A H 0.1226 0.4445 0.8699 0.048 Uiso 1 1 calc R . .
H12B H 0.2889 0.4594 0.9364 0.048 Uiso 1 1 calc R . .
H12C H 0.3163 0.4409 0.8274 0.048 Uiso 1 1 calc R . .
C13 C 0.59156(15) 0.86311(10) 0.91439(8) 0.0265(2) Uani 1 1 d . . .
H13A H 0.5233 0.8695 0.9726 0.032 Uiso 1 1 calc R . .
H13B H 0.6193 0.9397 0.8914 0.032 Uiso 1 1 calc R . .
C14 C 0.75835(16) 0.79435(11) 0.92933(9) 0.0330(3) Uani 1 1 d . . .
H14A H 0.8586 0.8440 0.9448 0.040 Uiso 1 1 calc R . .
H14B H 0.7425 0.7387 0.9799 0.040 Uiso 1 1 calc R . .
C15 C 0.78716(15) 0.73550(11) 0.83650(9) 0.0314(3) Uani 1 1 d . . .
H15A H 0.8464 0.7862 0.7918 0.038 Uiso 1 1 calc R . .
H15B H 0.8585 0.6664 0.8443 0.038 Uiso 1 1 calc R . .
C16 C 0.60257(17) 0.70686(11) 0.80411(9) 0.0334(3) Uani 1 1 d . . .
H16A H 0.5950 0.7069 0.7355 0.040 Uiso 1 1 calc R . .
H16B H 0.5653 0.6322 0.8277 0.040 Uiso 1 1 calc R . .
N1 N 0.49535(12) 0.79791(8) 0.84433(6) 0.0238(2) Uani 1 1 d . . .
O1 O 0.23564(12) 0.59458(7) 0.86067(6) 0.0294(2) Uani 1 1 d . . .
O2 O 0.24200(11) 0.89272(7) 0.86417(6) 0.0306(2) Uani 1 1 d . . .

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

C1 0.0185(5) 0.0186(4) 0.0198(5) -0.0017(3) 0.0013(4) 0.0018(4)
C2 0.0223(5) 0.0211(5) 0.0203(5) 0.0007(4) 0.0014(4) 0.0018(4)
C3 0.0254(5) 0.0172(4) 0.0291(5) -0.0019(4) 0.0021(4) -0.0029(4)
C4 0.0237(5) 0.0228(5) 0.0267(5) -0.0058(4) -0.0024(4) -0.0005(4)
C5 0.0211(5) 0.0223(5) 0.0218(5) -0.0025(4) 0.0000(4) 0.0014(4)
C6 0.0276(6) 0.0293(6) 0.0238(5) -0.0029(4) -0.0038(4) 0.0052(5)
C7 0.0336(6) 0.0302(6) 0.0217(5) 0.0032(4) 0.0001(4) 0.0078(5)
C8 0.0304(6) 0.0214(5) 0.0291(5) 0.0034(4) 0.0038(5) 0.0026(4)
C9 0.0248(5) 0.0198(4) 0.0256(5) -0.0006(4) 0.0012(4) 0.0003(4)
C10 0.0177(4) 0.0198(5) 0.0205(4) -0.0003(4) 0.0005(4) 0.0022(3)
C11 0.0232(5) 0.0180(4) 0.0196(4) 0.0000(4) -0.0006(4) 0.0009(4)
C12 0.0383(7) 0.0248(5) 0.0323(6) 0.0089(4) -0.0010(5) 0.0009(5)
C13 0.0236(5) 0.0275(5) 0.0282(5) -0.0059(4) -0.0032(4) 0.0002(4)
C14 0.0274(6) 0.0363(6) 0.0353(6) -0.0030(5) -0.0076(5) 0.0039(5)
C15 0.0220(5) 0.0337(6) 0.0384(6) -0.0009(5) 0.0032(5) 0.0043(4)
C16 0.0254(5) 0.0343(6) 0.0405(6) -0.0155(5) -0.0009(5) 0.0087(5)
N1 0.0224(4) 0.0238(4) 0.0251(4) -0.0069(3) -0.0016(4) 0.0035(3)
O1 0.0433(5) 0.0229(4) 0.0220(4) 0.0046(3) -0.0023(4) -0.0021(4)
O2 0.0295(4) 0.0288(4) 0.0334(4) -0.0115(3) -0.0048(4) 0.0095(3)

_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

C1 C2 1.3808(14) . ?
C1 C10 1.4222(14) . ?
C1 C11 1.5075(14) . ?
C2 O1 1.3722(13) . ?
C2 C3 1.4168(15) . ?
C3 C4 1.3632(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4187(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4212(16) . ?
C5 C10 1.4271(14) . ?
C6 C7 1.3702(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4141(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3717(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4247(14) . ?
C9 H9 0.9500 . ?
C11 O2 1.2304(13) . ?
C11 N1 1.3383(14) . ?
C12 O1 1.4265(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.4680(14) . ?
C13 C14 1.5264(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5246(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5217(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N1 1.4731(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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

C2 C1 C10 119.86(9) . . ?
C2 C1 C11 121.07(9) . . ?
C10 C1 C11 119.01(9) . . ?
O1 C2 C1 116.25(9) . . ?
O1 C2 C3 122.84(10) . . ?
C1 C2 C3 120.81(10) . . ?
C4 C3 C2 119.86(10) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.46(10) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 122.23(10) . . ?
C4 C5 C10 118.60(10) . . ?
C6 C5 C10 119.16(10) . . ?
C7 C6 C5 120.94(11) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.93(10) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.77(11) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.67(10) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C10 C9 122.16(10) . . ?
C1 C10 C5 119.33(9) . . ?
C9 C10 C5 118.50(10) . . ?
O2 C11 N1 122.62(10) . . ?
O2 C11 C1 120.48(9) . . ?
N1 C11 C1 116.86(9) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 103.44(9) . . ?
N1 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
N1 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
C15 C14 C13 103.93(10) . . ?
C15 C14 H14A 111.0 . . ?
C13 C14 H14A 111.0 . . ?
C15 C14 H14B 111.0 . . ?
C13 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
C16 C15 C14 103.75(9) . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
N1 C16 C15 103.28(9) . . ?
N1 C16 H16A 111.1 . . ?
C15 C16 H16A 111.1 . . ?
N1 C16 H16B 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C11 N1 C13 121.86(9) . . ?
C11 N1 C16 125.71(10) . . ?
C13 N1 C16 112.26(9) . . ?
C2 O1 C12 117.76(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

C10 C1 C2 O1 -179.31(9) . . . . ?
C11 C1 C2 O1 -2.28(14) . . . . ?
C10 C1 C2 C3 -2.70(15) . . . . ?
C11 C1 C2 C3 174.34(10) . . . . ?
O1 C2 C3 C4 178.47(10) . . . . ?
C1 C2 C3 C4 2.09(16) . . . . ?
C2 C3 C4 C5 0.45(17) . . . . ?
C3 C4 C5 C6 177.06(11) . . . . ?
C3 C4 C5 C10 -2.25(16) . . . . ?
C4 C5 C6 C7 -178.22(10) . . . . ?
C10 C5 C6 C7 1.09(16) . . . . ?
C5 C6 C7 C8 -1.64(18) . . . . ?
C6 C7 C8 C9 0.28(18) . . . . ?
C7 C8 C9 C10 1.63(17) . . . . ?
C2 C1 C10 C9 -177.62(9) . . . . ?
C11 C1 C10 C9 5.29(14) . . . . ?
C2 C1 C10 C5 0.83(14) . . . . ?
C11 C1 C10 C5 -176.26(9) . . . . ?
C8 C9 C10 C1 176.35(10) . . . . ?
C8 C9 C10 C5 -2.12(15) . . . . ?
C4 C5 C10 C1 1.60(14) . . . . ?
C6 C5 C10 C1 -177.74(10) . . . . ?
C4 C5 C10 C9 -179.89(9) . . . . ?
C6 C5 C10 C9 0.77(15) . . . . ?
C2 C1 C11 O2 -106.20(12) . . . . ?
C10 C1 C11 O2 70.86(13) . . . . ?
C2 C1 C11 N1 76.20(13) . . . . ?
C10 C1 C11 N1 -106.74(11) . . . . ?
N1 C13 C14 C15 28.68(12) . . . . ?
C13 C14 C15 C16 -37.02(12) . . . . ?
C14 C15 C16 N1 30.43(13) . . . . ?
O2 C11 N1 C13 3.35(16) . . . . ?
C1 C11 N1 C13 -179.11(9) . . . . ?
O2 C11 N1 C16 178.08(12) . . . . ?
C1 C11 N1 C16 -4.38(16) . . . . ?
C14 C13 N1 C11 165.49(10) . . . . ?
C14 C13 N1 C16 -9.89(13) . . . . ?
C15 C16 N1 C11 171.90(10) . . . . ?
C15 C16 N1 C13 -12.94(14) . . . . ?
C1 C2 O1 C12 -160.88(10) . . . . ?
C3 C2 O1 C12 22.58(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.953

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.318

_refine_diff_density_min         -0.294

_refine_diff_density_rms         0.088