# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
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data_(-)-(2R,3S)-2a
_database_code_depnum_ccdc_archive 'CCDC 869566'
#TrackingRef 'Org Lett 02-12.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common
;
SAW694 IC-1
;
_chemical_melting_point ?
_chemical_compound_source ?
_chemical_absolute_configuration ad
_chemical_formula_iupac ?
_chemical_formula_moiety 'C12 H17 N1 O3'
_chemical_formula_sum 'C12 H17 N1 O3'
_chemical_formula_weight 223.27
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'
_symmetry_cell_setting Orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_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'
_cell_length_a 7.5034(2)
_cell_length_b 12.2919(4)
_cell_length_c 13.0178(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1200.65(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 4898
_cell_measurement_theta_min 3.3922
_cell_measurement_theta_max 76.3036
_exptl_crystal_description lath
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.235
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 480
_exptl_absorpt_coefficient_mu 0.725
_exptl_absorpt_correction_T_min 0.57285
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5598
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11172
_diffrn_reflns_av_R_equivalents 0.0413
_diffrn_reflns_av_sigmaI/netI 0.0316
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 9.02
_diffrn_reflns_theta_max 74.39
_reflns_number_total 2448
_reflns_number_gt 2287
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution 'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2001), Mercury 2.4 (Macrae et al., 1998)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2001), Mercury 2.4 (Macrae et al., 1998)
;
_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^)+(0.0415P)^2^+0.1550P] 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 mixed
_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 -0.03(17)
_refine_ls_number_reflns 2448
_refine_ls_number_parameters 153
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0338
_refine_ls_R_factor_gt 0.0302
_refine_ls_wR_factor_ref 0.0760
_refine_ls_wR_factor_gt 0.0734
_refine_ls_goodness_of_fit_ref 1.006
_refine_ls_restrained_S_all 1.006
_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 0.02983(13) 0.46448(8) 0.20018(7) 0.0208(2) Uani 1 1 d . . .
H1A H -0.042(3) 0.4848(19) 0.1516(19) 0.046(6) Uiso 1 1 d . . .
O2 O 0.18347(13) 0.58536(9) 0.04930(7) 0.0251(2) Uani 1 1 d . . .
O3 O 0.36930(13) 0.66489(8) 0.16178(8) 0.0242(2) Uani 1 1 d . . .
N1 N -0.26218(15) 0.52063(9) 0.54829(9) 0.0223(2) Uani 1 1 d . . .
C1 C -0.00275(17) 0.61583(10) 0.48251(10) 0.0187(3) Uani 1 1 d . . .
C2 C 0.16238(19) 0.67909(12) 0.51061(11) 0.0251(3) Uani 1 1 d . . .
H2A H 0.1522 0.7536 0.4844 0.038 Uiso 1 1 calc R . .
H2B H 0.2671 0.6440 0.4802 0.038 Uiso 1 1 calc R . .
H2C H 0.1752 0.6808 0.5855 0.038 Uiso 1 1 calc R . .
C3 C -0.11015(18) 0.57544(11) 0.56143(10) 0.0211(3) Uani 1 1 d . . .
H3A H -0.0720 0.5880 0.6300 0.025 Uiso 1 1 calc R . .
C4 C -0.31369(17) 0.50382(11) 0.45048(11) 0.0221(3) Uani 1 1 d . . .
H4A H -0.4213 0.4651 0.4384 0.027 Uiso 1 1 calc R . .
C5 C -0.21701(18) 0.54037(11) 0.36683(10) 0.0213(3) Uani 1 1 d . . .
H5A H -0.2586 0.5260 0.2992 0.026 Uiso 1 1 calc R . .
C6 C -0.05918(17) 0.59807(10) 0.38104(9) 0.0176(3) Uani 1 1 d . . .
C7 C 0.04208(18) 0.64251(10) 0.28871(10) 0.0186(3) Uani 1 1 d . . .
H7A H 0.1331 0.6950 0.3149 0.022 Uiso 1 1 calc R . .
C8 C -0.08269(19) 0.70499(11) 0.21646(10) 0.0219(3) Uani 1 1 d . . .
H8A H -0.1555 0.7558 0.2565 0.033 Uiso 1 1 calc R . .
H8B H -0.1605 0.6535 0.1805 0.033 Uiso 1 1 calc R . .
H8C H -0.0118 0.7456 0.1662 0.033 Uiso 1 1 calc R . .
C9 C 0.14376(18) 0.54918(10) 0.23133(10) 0.0184(2) Uani 1 1 d . . .
C10 C 0.28409(18) 0.49782(12) 0.30065(10) 0.0225(3) Uani 1 1 d . . .
H10A H 0.3491 0.4418 0.2623 0.034 Uiso 1 1 calc R . .
H10B H 0.2258 0.4647 0.3603 0.034 Uiso 1 1 calc R . .
H10C H 0.3676 0.5539 0.3239 0.034 Uiso 1 1 calc R . .
C11 C 0.23241(17) 0.59990(11) 0.13658(10) 0.0190(3) Uani 1 1 d . . .
C12 C 0.4570(2) 0.71678(13) 0.07555(11) 0.0275(3) Uani 1 1 d . . .
H12A H 0.5533 0.7636 0.1008 0.041 Uiso 1 1 calc R . .
H12B H 0.3705 0.7609 0.0375 0.041 Uiso 1 1 calc R . .
H12C H 0.5067 0.6610 0.0300 0.041 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
O1 0.0259(5) 0.0172(4) 0.0194(4) -0.0003(3) -0.0013(4) -0.0020(4)
O2 0.0285(5) 0.0311(5) 0.0156(4) -0.0005(4) -0.0002(4) -0.0021(4)
O3 0.0252(5) 0.0278(5) 0.0195(4) 0.0039(4) 0.0002(4) -0.0065(4)
N1 0.0226(5) 0.0223(5) 0.0219(5) 0.0038(5) 0.0024(4) 0.0012(5)
C1 0.0223(6) 0.0158(6) 0.0180(6) 0.0005(4) -0.0011(5) 0.0004(5)
C2 0.0289(7) 0.0282(7) 0.0183(6) -0.0013(5) -0.0038(5) -0.0071(6)
C3 0.0253(6) 0.0211(6) 0.0170(6) 0.0019(5) -0.0009(5) 0.0016(5)
C4 0.0204(6) 0.0216(6) 0.0243(6) 0.0010(5) -0.0003(5) -0.0013(5)
C5 0.0217(6) 0.0226(6) 0.0197(6) -0.0020(5) -0.0017(5) -0.0006(5)
C6 0.0198(6) 0.0160(6) 0.0170(6) -0.0005(5) 0.0005(5) 0.0021(5)
C7 0.0212(6) 0.0179(6) 0.0168(6) 0.0000(5) -0.0009(5) -0.0012(5)
C8 0.0287(7) 0.0184(6) 0.0186(6) 0.0011(5) -0.0006(5) 0.0049(5)
C9 0.0202(6) 0.0193(6) 0.0157(5) 0.0016(5) 0.0003(5) -0.0003(5)
C10 0.0224(6) 0.0262(7) 0.0188(6) 0.0022(5) -0.0012(5) 0.0032(5)
C11 0.0192(6) 0.0190(6) 0.0186(6) 0.0004(5) 0.0002(5) 0.0020(5)
C12 0.0281(7) 0.0288(7) 0.0255(7) 0.0076(5) 0.0050(6) -0.0038(6)
_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 C9 1.4068(16) . y
O1 H1A 0.87(2) . y
O2 C11 1.2074(17) . y
O3 C11 1.3419(16) . y
O3 C12 1.4492(16) . y
N1 C3 1.3359(19) . y
N1 C4 1.3465(18) . y
C1 C3 1.3969(19) . y
C1 C6 1.4042(18) . y
C1 C2 1.5079(18) . y
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9500 . ?
C4 C5 1.3835(19) . y
C4 H4A 0.9500 . ?
C5 C6 1.3928(19) . y
C5 H5A 0.9500 . ?
C6 C7 1.5232(17) . y
C7 C8 1.5332(17) . y
C7 C9 1.5672(18) . y
C7 H7A 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5237(18) . y
C9 C11 1.5339(17) . y
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C9 O1 H1A 111.9(16) . . y
C11 O3 C12 114.86(11) . . y
C3 N1 C4 116.33(11) . . y
C3 C1 C6 117.56(12) . . y
C3 C1 C2 118.61(12) . . y
C6 C1 C2 123.79(12) . . y
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C1 125.29(13) . . y
N1 C3 H3A 117.4 . . ?
C1 C3 H3A 117.4 . . ?
N1 C4 C5 122.96(12) . . y
N1 C4 H4A 118.5 . . ?
C5 C4 H4A 118.5 . . ?
C4 C5 C6 120.44(12) . . y
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 117.42(12) . . y
C5 C6 C7 120.13(11) . . y
C1 C6 C7 122.42(12) . . y
C6 C7 C8 111.05(11) . . y
C6 C7 C9 110.88(10) . . y
C8 C7 C9 111.81(10) . . y
C6 C7 H7A 107.6 . . ?
C8 C7 H7A 107.6 . . ?
C9 C7 H7A 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C10 106.50(11) . . y
O1 C9 C11 109.42(10) . . y
C10 C9 C11 110.18(11) . . y
O1 C9 C7 112.54(10) . . y
C10 C9 C7 110.94(10) . . y
C11 C9 C7 107.27(10) . . y
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O3 123.44(12) . . y
O2 C11 C9 124.38(12) . . y
O3 C11 C9 112.17(11) . . y
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 C3 C1 0.0(2) . . . . y
C6 C1 C3 N1 0.4(2) . . . . y
C2 C1 C3 N1 178.17(13) . . . . y
C3 N1 C4 C5 0.02(19) . . . . y
N1 C4 C5 C6 -0.4(2) . . . . y
C4 C5 C6 C1 0.79(19) . . . . y
C4 C5 C6 C7 -177.20(12) . . . . y
C3 C1 C6 C5 -0.74(18) . . . . y
C2 C1 C6 C5 -178.42(12) . . . . y
C3 C1 C6 C7 177.20(12) . . . . y
C2 C1 C6 C7 -0.48(19) . . . . y
C5 C6 C7 C8 49.36(15) . . . . y
C1 C6 C7 C8 -128.53(13) . . . . y
C5 C6 C7 C9 -75.59(14) . . . . y
C1 C6 C7 C9 106.52(14) . . . . y
C6 C7 C9 O1 56.40(14) . . . . y
C8 C7 C9 O1 -68.12(14) . . . . y
C6 C7 C9 C10 -62.82(14) . . . . y
C8 C7 C9 C10 172.66(11) . . . . y
C6 C7 C9 C11 176.80(10) . . . . y
C8 C7 C9 C11 52.28(14) . . . . y
C12 O3 C11 O2 -0.47(19) . . . . y
C12 O3 C11 C9 -179.05(11) . . . . y
O1 C9 C11 O2 14.54(18) . . . . y
C10 C9 C11 O2 131.31(14) . . . . y
C7 C9 C11 O2 -107.82(14) . . . . y
O1 C9 C11 O3 -166.90(10) . . . . y
C10 C9 C11 O3 -50.12(14) . . . . y
C7 C9 C11 O3 70.74(13) . . . . y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N1 0.87(2) 2.00(2) 2.8242(15) 160(2) 2_464 y
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 74.39
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.152
_refine_diff_density_min -0.157
_refine_diff_density_rms 0.033
data_(+)-(2S,3S)-2b
_database_code_depnum_ccdc_archive 'CCDC 869567'
#TrackingRef 'Org Lett 02-12.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H17 N O3'
_chemical_formula_sum 'C12 H17 N O3'
_chemical_formula_weight 223.27
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'
_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 5.97836(4)
_cell_length_b 12.67070(7)
_cell_length_c 15.76352(9)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1194.087(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 173
_cell_measurement_reflns_used 38525
_cell_measurement_theta_min 2.8009
_cell_measurement_theta_max 72.3262
_exptl_crystal_description shards
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.242
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 480
_exptl_absorpt_coefficient_mu 0.729
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.839
_exptl_absorpt_correction_T_max 0.939
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'OD Xcalibur PX Ultra'
_diffrn_measurement_method 'omega scans'
_diffrn_detector_area_resol_mean 8.2556
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 44547
_diffrn_reflns_av_R_equivalents 0.0283
_diffrn_reflns_av_sigmaI/netI 0.0076
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 4.48
_diffrn_reflns_theta_max 72.48
_reflns_number_total 2366
_reflns_number_gt 2337
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd'
_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.
Results of chirality/polarity tests
_refine_ls_R_factor_obs+ 0.0262
_refine_ls_wR_factor_obs+ 0.0723
_refine_ls_abs_structure_Flack+ 0.00(16)
_refine_ls_R_factor_obs- 0.0264
_refine_ls_wR_factor_obs- 0.0729
_refine_ls_abs_structure_Flack- 1.05(16)
;
_chemical_absolute_configuration ad
_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^)+(0.0444P)^2^+0.1449P] 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 mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0157(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 967 Friedel pairs'
_refine_ls_abs_structure_Flack -0.05(16)
_refine_ls_number_reflns 2366
_refine_ls_number_parameters 152
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0264
_refine_ls_R_factor_gt 0.0262
_refine_ls_wR_factor_ref 0.0726
_refine_ls_wR_factor_gt 0.0723
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_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
N1 N 0.2477(2) 0.47905(8) 0.88035(6) 0.0379(2) Uani 1 1 d . . .
C2 C 0.4275(2) 0.54026(9) 0.88713(7) 0.0357(3) Uani 1 1 d . . .
H2A H 0.4875 0.5505 0.9423 0.043 Uiso 1 1 calc R . .
C3 C 0.53481(19) 0.59040(8) 0.82019(6) 0.0305(2) Uani 1 1 d . . .
C4 C 0.44423(19) 0.57645(8) 0.73849(6) 0.0270(2) Uani 1 1 d . . .
C5 C 0.2538(2) 0.51402(9) 0.73099(7) 0.0320(2) Uani 1 1 d . . .
H5A H 0.1861 0.5039 0.6771 0.038 Uiso 1 1 calc R . .
C6 C 0.1629(2) 0.46664(10) 0.80248(7) 0.0366(3) Uani 1 1 d . . .
H6A H 0.0344 0.4233 0.7958 0.044 Uiso 1 1 calc R . .
C7 C 0.7350(2) 0.65823(10) 0.83850(8) 0.0404(3) Uani 1 1 d . . .
H7A H 0.7909 0.6427 0.8956 0.061 Uiso 1 1 calc R . .
H7B H 0.6923 0.7328 0.8351 0.061 Uiso 1 1 calc R . .
H7C H 0.8525 0.6435 0.7968 0.061 Uiso 1 1 calc R . .
C8 C 0.54528(19) 0.63412(8) 0.66347(6) 0.0291(2) Uani 1 1 d . . .
H8A H 0.7094 0.6408 0.6745 0.035 Uiso 1 1 calc R . .
C9 C 0.51755(17) 0.57986(9) 0.57600(6) 0.0273(2) Uani 1 1 d . . .
C10 C 0.56549(19) 0.46082(8) 0.58074(6) 0.0287(2) Uani 1 1 d . . .
O10 O 0.44277(16) 0.39269(6) 0.55593(6) 0.0425(2) Uani 1 1 d . . .
O11 O 0.76992(15) 0.44240(6) 0.61221(6) 0.0416(2) Uani 1 1 d . . .
C12 C 0.8440(3) 0.33381(10) 0.61121(10) 0.0507(3) Uani 1 1 d . . .
H12A H 0.7997 0.3008 0.5576 0.076 Uiso 1 1 calc R . .
H12B H 0.7753 0.2956 0.6586 0.076 Uiso 1 1 calc R . .
H12C H 1.0072 0.3314 0.6168 0.076 Uiso 1 1 calc R . .
C13 C 0.4480(3) 0.74640(9) 0.66133(7) 0.0414(3) Uani 1 1 d . . .
H13A H 0.4675 0.7797 0.7170 0.062 Uiso 1 1 calc R . .
H13B H 0.2883 0.7431 0.6475 0.062 Uiso 1 1 calc R . .
H13C H 0.5261 0.7881 0.6181 0.062 Uiso 1 1 calc R . .
O14 O 0.29596(13) 0.59515(6) 0.54764(5) 0.03130(19) Uani 1 1 d D . .
H14 H 0.289(3) 0.5731(14) 0.4934(4) 0.062(5) Uiso 1 1 d D . .
C15 C 0.6838(2) 0.62686(9) 0.51219(7) 0.0359(3) Uani 1 1 d . . .
H15A H 0.6652 0.5921 0.4571 0.054 Uiso 1 1 calc R . .
H15B H 0.8368 0.6158 0.5326 0.054 Uiso 1 1 calc R . .
H15C H 0.6556 0.7027 0.5061 0.054 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
N1 0.0484(6) 0.0400(5) 0.0254(4) 0.0037(4) 0.0066(4) 0.0029(5)
C2 0.0487(7) 0.0363(5) 0.0221(5) -0.0004(4) -0.0024(5) 0.0068(5)
C3 0.0371(6) 0.0291(5) 0.0253(5) -0.0013(4) -0.0044(4) 0.0039(4)
C4 0.0318(5) 0.0269(5) 0.0224(4) 0.0003(4) -0.0014(4) 0.0030(4)
C5 0.0340(6) 0.0375(5) 0.0244(5) 0.0004(4) 0.0002(4) -0.0021(5)
C6 0.0378(6) 0.0421(6) 0.0299(5) 0.0021(5) 0.0043(5) -0.0040(5)
C7 0.0450(6) 0.0431(6) 0.0331(6) -0.0048(5) -0.0117(5) -0.0024(5)
C8 0.0325(5) 0.0314(5) 0.0235(5) 0.0015(4) -0.0025(4) -0.0049(4)
C9 0.0288(5) 0.0299(5) 0.0232(5) 0.0020(4) 0.0001(4) -0.0012(4)
C10 0.0303(5) 0.0324(5) 0.0234(4) 0.0024(4) 0.0018(4) -0.0012(5)
O10 0.0458(5) 0.0331(4) 0.0486(5) -0.0023(4) -0.0080(4) -0.0048(4)
O11 0.0353(4) 0.0343(4) 0.0553(5) 0.0017(4) -0.0089(4) 0.0041(3)
C12 0.0492(7) 0.0380(6) 0.0650(9) 0.0066(6) -0.0026(7) 0.0118(6)
C13 0.0675(8) 0.0289(5) 0.0280(5) 0.0001(4) -0.0011(6) -0.0014(6)
O14 0.0313(4) 0.0397(4) 0.0230(3) -0.0024(3) -0.0037(3) 0.0039(3)
C15 0.0403(6) 0.0370(6) 0.0303(5) 0.0051(4) 0.0072(5) -0.0025(5)
_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
N1 C2 1.3299(18) . ?
N1 C6 1.3372(16) . ?
C2 C3 1.3888(16) . ?
C3 C4 1.4083(14) . ?
C3 C7 1.5014(17) . ?
C4 C5 1.3915(16) . ?
C4 C8 1.5158(14) . ?
C5 C6 1.3877(15) . ?
C8 C13 1.5373(16) . ?
C8 C9 1.5496(14) . ?
C9 O14 1.4115(12) . ?
C9 C15 1.5345(15) . ?
C9 C10 1.5371(15) . ?
C10 O10 1.1985(14) . ?
C10 O11 1.3395(14) . ?
O11 C12 1.4454(15) . ?
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 N1 C6 116.67(10) . . ?
N1 C2 C3 125.38(10) . . ?
C2 C3 C4 117.38(10) . . ?
C2 C3 C7 118.95(10) . . ?
C4 C3 C7 123.65(10) . . ?
C5 C4 C3 117.63(9) . . ?
C5 C4 C8 122.27(9) . . ?
C3 C4 C8 119.98(10) . . ?
C6 C5 C4 119.82(10) . . ?
N1 C6 C5 123.10(11) . . ?
C4 C8 C13 108.21(9) . . ?
C4 C8 C9 115.95(8) . . ?
C13 C8 C9 110.53(9) . . ?
O14 C9 C15 110.30(8) . . ?
O14 C9 C10 108.97(9) . . ?
C15 C9 C10 106.97(9) . . ?
O14 C9 C8 108.75(8) . . ?
C15 C9 C8 109.99(9) . . ?
C10 C9 C8 111.85(8) . . ?
O10 C10 O11 123.63(10) . . ?
O10 C10 C9 125.23(10) . . ?
O11 C10 C9 111.04(9) . . ?
C10 O11 C12 116.19(10) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 72.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.161
_refine_diff_density_min -0.104
_refine_diff_density_rms 0.028
#===END