# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
#TrackingRef '5768_web_deposit_cif_file_0_Pascal_1307444959.za231_todeposit.cif'
_audit_creation_date 30-05-11
_publ_contact_author_name
;
JOSEPH, Delphine
;
_publ_contact_author_address
;
UMR CNRS 8076 BioCIS
IPSIT
UFR de Pharmacie, UPS-11, Tour D3 2e Etage
5, Rue J.-B. Cl\'ement
92296 Ch\^atenay-Malabry cedex
France
;
_publ_contact_author_phone '+33 (0)1 46 83 57 30'
_publ_contact_author_fax +33146....
_publ_contact_author_email delphine.joseph@u-psud.fr
_publ_contact_letter
;
;
_publ_requested_category FM
_publ_section_title
;
Routes to ................
..........................
..........................
;
loop_
_publ_author_name
_publ_author_address
Z.Amara
;UMR CNRS 8076 BioCIS
IPSIT
UFR de Pharmacie, UPS-11, Tour D3 2e Etage
5, Rue J.-B. Cl\'ement
92296 Ch\^atenay-Malabry cedex
France
;
E.Drege
;Centre de Recherches de Gif
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
C.Troufflard
;UMR CNRS 8076 BioCIS
IPSIT
UFR de Pharmacie, UPS-11, Tour D3 2e Etage
5, Rue J.-B. Cl\'ement
92296 Ch\^atenay-Malabry cedex
France
;
P.Retailleau ''
D.Joseph ''
_publ_section_abstract
; ?
;
_publ_section_comment
; ?
;
_publ_section_exptl_prep
; ?
;
_publ_section_exptl_refinement
; ?
;
_publ_section_references
;
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P.,
Taylor, R., Towler, M. & van de Streek, J. (2006). Mercury: visualization and
analysis of crystal structures. J.Appl. Cryst. 39, 453-457.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Volume 276,
Macromolecular Crystallography, part A, edited by C.W. Carter, Jr. & R.M.
Sweet, 307-326, 1997, New York: Academic Press.
Sheldrick, G.M. (2008).Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J.Appl. Cryst. 36, 7-13.
Welter, R. (2006). The Crystalbuilder Project
Acta Cryst. A62, s252.
Westrip, S. P. (2010). publCIF:: software for editing, validating and formatting
crystallographic information filesJ. Appl. Cryst. 43, 920-925.
;
_publ_section_figure_captions
; ?
;
_publ_section_acknowledgements
; ?
;
data_za231
_database_code_depnum_ccdc_archive 'CCDC 828848'
#TrackingRef '5768_web_deposit_cif_file_0_Pascal_1307444959.za231_todeposit.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(meso)1-methyl-2,5-diphenethylpyrrolidin-1-ium chloride
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H28 N, Cl'
_chemical_formula_sum 'C21 H28 Cl N'
_chemical_formula_weight 329.89
_chemical_absolute_configuration ad
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'
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 'A b a 2'
_symmetry_space_group_name_Hall 'A 2 -2ac'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, z+1/2'
_cell_length_a 25.438(2)
_cell_length_b 10.6710(5)
_cell_length_c 7.1250(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1934.07(19)
_cell_formula_units_Z 4
_cell_measurement_temperature 200(2)
_cell_measurement_reflns_used 9798
_cell_measurement_theta_min 6.6
_cell_measurement_theta_max 71.6
_exptl_crystal_description 'regular parallelepiped'
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.16
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.133
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 712
_exptl_absorpt_coefficient_mu 1.721
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.680
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 200(2)
_diffrn_radiation_wavelength 1.54187
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 12865
_diffrn_reflns_av_R_equivalents 0.0375
_diffrn_reflns_av_sigmaI/netI 0.0261
_diffrn_reflns_limit_h_min -31
_diffrn_reflns_limit_h_max 31
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 6.96
_diffrn_reflns_theta_max 73.14
_reflns_number_total 1894
_reflns_number_gt 1405
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_molecular_graphics 'PLATON (Spek, 2003)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_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^)+(0.1146P)^2^+0.0000P] 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; 855 Friedel pairs'
_refine_ls_abs_structure_Flack -0.01(5)
_refine_ls_number_reflns 1891
_refine_ls_number_parameters 131
_refine_ls_number_restraints 4
_refine_ls_R_factor_all 0.0718
_refine_ls_R_factor_gt 0.0544
_refine_ls_wR_factor_ref 0.1763
_refine_ls_wR_factor_gt 0.1467
_refine_ls_goodness_of_fit_ref 1.136
_refine_ls_restrained_S_all 1.307
_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 1.0000 0.0000 0.0235(3) 0.0793(4) Uani 1 2 d S . .
N1 N 1.0155(2) 0.0443(6) 0.4466(8) 0.0561(11) Uani 0.50 1 d P . .
H1 H 1.0135 0.0381 0.3166 0.067 Uiso 0.50 1 calc PR . .
C2 C 0.96423(11) 0.0686(3) 0.5235(5) 0.0685(8) Uani 1 1 d D A .
H2 H 0.9670 0.0971 0.6568 0.082 Uiso 1 1 calc R . .
C3 C 0.9839(3) -0.1449(7) 0.4900(14) 0.093(3) Uani 0.50 1 d PD . .
H3A H 0.9842 -0.1814 0.3623 0.111 Uiso 0.50 1 calc PR . .
H3B H 0.9817 -0.2145 0.5816 0.111 Uiso 0.50 1 calc PR . .
C4 C 0.9362(3) -0.0590(8) 0.5121(18) 0.088(2) Uani 0.50 1 d PD . .
H4A H 0.9162 -0.0777 0.6281 0.106 Uiso 0.50 1 calc PR . .
H4B H 0.9124 -0.0639 0.4024 0.106 Uiso 0.50 1 calc PR . .
C6 C 0.9487(4) -0.1465(9) 0.5003(15) 0.086(2) Uani 0.50 1 d P . .
H6A H 0.9542 -0.1678 0.6326 0.129 Uiso 0.50 1 calc PR . .
H6B H 0.9558 -0.2202 0.4222 0.129 Uiso 0.50 1 calc PR . .
H6C H 0.9122 -0.1196 0.4817 0.129 Uiso 0.50 1 calc PR . .
C7 C 0.92515(14) 0.1455(4) 0.4199(4) 0.0943(14) Uani 1 1 d D . .
H7A H 0.9428 0.1763 0.3050 0.113 Uiso 0.548(12) 1 calc PR A 1
H7B H 0.8970 0.0878 0.3781 0.113 Uiso 0.548(12) 1 calc PR A 1
H7C H 0.9437 0.2216 0.3761 0.113 Uiso 0.452(12) 1 calc PR A 2
H7D H 0.9153 0.0976 0.3062 0.113 Uiso 0.452(12) 1 calc PR A 2
C8A C 0.90031(14) 0.2491(4) 0.5026(4) 0.077(2) Uani 0.548(12) 1 d P A 1
H8A1 H 0.9265 0.3173 0.5135 0.093 Uiso 0.548(12) 1 calc PR A 1
H8A2 H 0.8898 0.2253 0.6315 0.093 Uiso 0.548(12) 1 calc PR A 1
C8B C 0.8769(3) 0.1866(10) 0.5064(14) 0.078(3) Uani 0.452(12) 1 d P A 2
H8B1 H 0.8839 0.2094 0.6388 0.093 Uiso 0.452(12) 1 calc PR A 2
H8B2 H 0.8513 0.1166 0.5060 0.093 Uiso 0.452(12) 1 calc PR A 2
C9 C 0.85251(12) 0.3008(4) 0.4037(5) 0.0781(10) Uani 1 1 d . . .
C10 C 0.85208(15) 0.4267(5) 0.4335(8) 0.0963(12) Uani 1 1 d . A .
H10 H 0.8757 0.4629 0.5214 0.116 Uiso 1 1 calc R . .
C11 C 0.8178(4) 0.5007(5) 0.3374(12) 0.126(2) Uani 1 1 d . . .
H11 H 0.8170 0.5881 0.3625 0.152 Uiso 1 1 calc R A .
C12 C 0.7863(3) 0.4548(9) 0.2127(12) 0.144(3) Uani 1 1 d . A .
H12 H 0.7636 0.5092 0.1448 0.173 Uiso 1 1 calc R . .
C13 C 0.7852(2) 0.3290(8) 0.1774(10) 0.136(2) Uani 1 1 d . . .
H13 H 0.7621 0.2951 0.0858 0.163 Uiso 1 1 calc R A .
C14 C 0.81823(16) 0.2532(5) 0.2772(8) 0.1012(12) Uani 1 1 d . A .
H14 H 0.8171 0.1652 0.2574 0.121 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 0.0838(6) 0.1146(11) 0.0397(5) 0.000 0.000 0.0059(5)
N1 0.070(3) 0.056(3) 0.042(2) -0.007(2) -0.008(2) 0.003(2)
C2 0.0866(17) 0.075(2) 0.0440(13) -0.007(2) -0.0020(18) 0.0161(17)
C3 0.076(4) 0.118(8) 0.084(7) 0.007(6) 0.012(4) 0.006(5)
C4 0.095(5) 0.067(5) 0.102(6) 0.015(6) 0.026(5) -0.004(4)
C6 0.084(5) 0.081(6) 0.092(6) 0.008(5) 0.017(5) -0.021(5)
C7 0.102(2) 0.132(4) 0.0490(17) 0.004(2) 0.0021(17) 0.052(2)
C8A 0.090(5) 0.078(5) 0.064(4) -0.019(4) 0.002(3) 0.022(4)
C8B 0.075(4) 0.090(7) 0.069(5) 0.027(5) 0.020(4) 0.018(4)
C9 0.0763(18) 0.094(3) 0.0636(18) -0.0001(18) 0.0105(14) 0.0213(19)
C10 0.090(2) 0.111(4) 0.088(3) -0.010(3) 0.004(2) -0.002(2)
C11 0.177(7) 0.094(4) 0.109(5) 0.005(3) 0.015(4) 0.028(3)
C12 0.154(6) 0.154(6) 0.126(5) 0.012(5) -0.023(4) 0.075(5)
C13 0.087(3) 0.196(7) 0.124(4) -0.020(5) -0.034(3) 0.019(4)
C14 0.103(3) 0.097(3) 0.104(3) -0.012(3) -0.010(3) -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
N1 C2 1.420(7) 2_755 ?
N1 C2 1.437(6) . ?
N1 C6 1.473(9) 2_755 ?
N1 H1 0.9300 . ?
C2 C7 1.485(4) . ?
C2 C4 1.539(10) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(7) . ?
C3 C2 1.569(10) 2_755 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 N1 1.473(9) 2_755 ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8A 1.4030 . ?
C7 C8B 1.443(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H7C 0.9900 . ?
C7 H7D 0.9900 . ?
C8A C9 1.510(5) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C8B C9 1.551(9) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9 C14 1.353(6) . ?
C9 C10 1.360(6) . ?
C10 C11 1.362(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.292(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.366(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
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 C2 109.6(4) 2_755 . ?
C2 N1 C6 107.6(6) 2_755 2_755 ?
C2 N1 C6 109.2(6) . 2_755 ?
C2 N1 H1 110.1 2_755 . ?
C2 N1 H1 110.1 . . ?
C6 N1 H1 110.1 2_755 . ?
N1 C2 C7 121.1(4) . . ?
N1 C2 C4 103.9(4) . . ?
C7 C2 C4 98.8(5) . . ?
N1 C2 H2 110.6 . . ?
C7 C2 H2 110.6 . . ?
C4 C2 H2 110.6 . . ?
C4 C3 C2 109.9(6) . 2_755 ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 2_755 . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 2_755 . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C2 99.7(5) . . ?
C3 C4 H4A 111.8 . . ?
C2 C4 H4A 111.8 . . ?
C3 C4 H4B 111.8 . . ?
C2 C4 H4B 111.8 . . ?
H4A C4 H4B 109.6 . . ?
N1 C6 H6A 109.5 2_755 . ?
N1 C6 H6B 109.5 2_755 . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 2_755 . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8A C7 C8B 36.6(5) . . ?
C8A C7 C2 121.86(19) . . ?
C8B C7 C2 121.7(4) . . ?
C8A C7 H7A 106.9 . . ?
C8B C7 H7A 129.7 . . ?
C2 C7 H7A 106.9 . . ?
C8A C7 H7B 106.9 . . ?
C8B C7 H7B 72.6 . . ?
C2 C7 H7B 106.9 . . ?
H7A C7 H7B 106.7 . . ?
C8A C7 H7C 72.6 . . ?
C8B C7 H7C 106.9 . . ?
C2 C7 H7C 106.9 . . ?
H7A C7 H7C 41.4 . . ?
H7B C7 H7C 139.5 . . ?
C8A C7 H7D 129.5 . . ?
C8B C7 H7D 106.9 . . ?
C2 C7 H7D 106.9 . . ?
H7A C7 H7D 67.1 . . ?
H7B C7 H7D 41.4 . . ?
H7C C7 H7D 106.7 . . ?
C7 C8A C9 117.0(2) . . ?
C7 C8A H8A1 108.0 . . ?
C9 C8A H8A1 108.0 . . ?
C7 C8A H8A2 108.0 . . ?
C9 C8A H8A2 108.0 . . ?
H8A1 C8A H8A2 107.3 . . ?
C7 C8B C9 112.2(5) . . ?
C7 C8B H8B1 109.2 . . ?
C9 C8B H8B1 109.2 . . ?
C7 C8B H8B2 109.2 . . ?
C9 C8B H8B2 109.2 . . ?
H8B1 C8B H8B2 107.9 . . ?
C14 C9 C10 118.0(4) . . ?
C14 C9 C8A 133.9(4) . . ?
C10 C9 C8A 107.1(4) . . ?
C14 C9 C8B 106.1(6) . . ?
C10 C9 C8B 134.9(6) . . ?
C8A C9 C8B 34.0(4) . . ?
C9 C10 C11 120.0(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 121.5(6) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.7(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 118.3(6) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C9 C14 C13 121.4(5) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
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
C2 N1 C2 C7 -154.9(4) 2_755 . . . ?
C6 N1 C2 C7 87.5(7) 2_755 . . . ?
C2 N1 C2 C4 -45.4(7) 2_755 . . . ?
C6 N1 C2 C4 -163.1(6) 2_755 . . . ?
C2 C3 C4 C2 9.5(10) 2_755 . . . ?
N1 C2 C4 C3 18.5(9) . . . . ?
C7 C2 C4 C3 143.7(7) . . . . ?
N1 C2 C7 C8A -127.0(4) . . . . ?
C4 C2 C7 C8A 120.8(4) . . . . ?
N1 C2 C7 C8B -170.4(7) . . . . ?
C4 C2 C7 C8B 77.4(8) . . . . ?
C8B C7 C8A C9 -64.1(7) . . . . ?
C2 C7 C8A C9 -165.6(4) . . . . ?
C8A C7 C8B C9 57.4(6) . . . . ?
C2 C7 C8B C9 159.5(6) . . . . ?
C7 C8A C9 C14 20.9(5) . . . . ?
C7 C8A C9 C10 -147.0(2) . . . . ?
C7 C8A C9 C8B 63.3(7) . . . . ?
C7 C8B C9 C14 92.9(8) . . . . ?
C7 C8B C9 C10 -99.5(8) . . . . ?
C7 C8B C9 C8A -56.7(5) . . . . ?
C14 C9 C10 C11 0.0(7) . . . . ?
C8A C9 C10 C11 170.1(5) . . . . ?
C8B C9 C10 C11 -166.5(6) . . . . ?
C9 C10 C11 C12 -2.2(11) . . . . ?
C10 C11 C12 C13 2.1(13) . . . . ?
C11 C12 C13 C14 0.0(12) . . . . ?
C10 C9 C14 C13 2.1(7) . . . . ?
C8A C9 C14 C13 -164.7(5) . . . . ?
C8B C9 C14 C13 172.2(6) . . . . ?
C12 C13 C14 C9 -2.2(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 73.14
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 0.281
_refine_diff_density_min -0.353
_refine_diff_density_rms 0.051
data_compound_13d
_database_code_depnum_ccdc_archive 'CCDC 854591'
#TrackingRef '- compound13d_final.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2,2'-(1-benzhydryl-2,5-dihydro-1H-pyrrole-2,5-diyl)bis(1-phenylethanone)
;
_chemical_name_common
;2,2'-(1-benzhydryl-2,5-dihydro-1H-pyrrole-2,5-diyl)bis(1-
phenylethanone)
;
_chemical_melting_point ?
_chemical_formula_moiety 'C33 H29 N O2'
_chemical_formula_sum 'C33 H29 N O2'
_chemical_formula_weight 471.57
_chemical_absolute_configuration .
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 'P b c m'
_symmetry_space_group_name_Hall '-P 2c 2b'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, z'
'x, -y-1/2, z-1/2'
_cell_length_a 8.806(4)
_cell_length_b 11.377(5)
_cell_length_c 26.118(8)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2616.7(18)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 2080
_cell_measurement_theta_min 0.998
_cell_measurement_theta_max 23.257
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.46
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.197
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1000
_exptl_absorpt_coefficient_mu 0.074
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.89
_exptl_absorpt_correction_T_max 0.99
_exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius kappa-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 11516
_diffrn_reflns_av_R_equivalents 0.0245
_diffrn_reflns_av_sigmaI/netI 0.0326
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 1.56
_diffrn_reflns_theta_max 23.29
_reflns_number_total 1919
_reflns_number_gt 1361
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR97 (Altomare et al, 1999)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_molecular_graphics 'PLATON (Spek, 2003)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_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^)+(0.1040P)^2^+0.8249P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 1919
_refine_ls_number_parameters 167
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0885
_refine_ls_R_factor_gt 0.0635
_refine_ls_wR_factor_ref 0.1925
_refine_ls_wR_factor_gt 0.1708
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_restrained_S_all 1.050
_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 0.5945(3) -0.0577(4) 0.36782(12) 0.1716(17) Uani 1 1 d . . .
N1 N 0.2503(3) 0.0791(2) 0.2500 0.0532(8) Uani 1 2 d S . .
C1 C 0.0866(4) 0.1042(3) 0.2500 0.0564(10) Uani 1 2 d S . .
H1 H 0.0329 0.0288 0.2500 0.068 Uiso 1 2 calc SR . .
C2 C 0.0386(3) 0.1710(2) 0.29773(9) 0.0560(7) Uani 1 1 d . . .
C3 C 0.1144(3) 0.2688(2) 0.31602(10) 0.0654(8) Uani 1 1 d . . .
H3 H 0.2004 0.2955 0.2989 0.079 Uiso 1 1 calc R . .
C4 C 0.0646(4) 0.3277(2) 0.35940(11) 0.0752(9) Uani 1 1 d . . .
H4 H 0.1177 0.3927 0.3715 0.090 Uiso 1 1 calc R . .
C5 C -0.0631(4) 0.2896(3) 0.38418(12) 0.0820(10) Uani 1 1 d . . .
H5 H -0.0969 0.3285 0.4133 0.098 Uiso 1 1 calc R . .
C6 C -0.1405(4) 0.1952(3) 0.36630(12) 0.0845(10) Uani 1 1 d . . .
H6 H -0.2280 0.1705 0.3830 0.101 Uiso 1 1 calc R . .
C7 C -0.0909(3) 0.1356(2) 0.32360(12) 0.0717(9) Uani 1 1 d . . .
H7 H -0.1450 0.0707 0.3120 0.086 Uiso 1 1 calc R . .
C8 C 0.2992(3) 0.0111(2) 0.29573(9) 0.0563(7) Uani 1 1 d . . .
H8 H 0.2137 0.0048 0.3196 0.068 Uiso 1 1 calc R . .
C9 C 0.3392(5) -0.1101(3) 0.27608(13) 0.1224(16) Uani 1 1 d . . .
H9 H 0.3605 -0.1749 0.2966 0.147 Uiso 1 1 calc R . .
C10 C 0.4320(4) 0.0713(3) 0.32269(13) 0.0952(12) Uani 1 1 d . . .
H10A H 0.5168 0.0781 0.2992 0.114 Uiso 1 1 calc R . .
H10B H 0.4021 0.1499 0.3329 0.114 Uiso 1 1 calc R . .
C11 C 0.4805(4) 0.0025(4) 0.36919(15) 0.0983(12) Uani 1 1 d . . .
C12 C 0.3843(4) 0.0027(3) 0.41591(12) 0.0765(10) Uani 1 1 d . . .
C13 C 0.2771(5) 0.0863(3) 0.42515(15) 0.1084(13) Uani 1 1 d . . .
H13 H 0.2604 0.1455 0.4012 0.130 Uiso 1 1 calc R . .
C14 C 0.1923(6) 0.0841(4) 0.47003(18) 0.1349(18) Uani 1 1 d . . .
H14 H 0.1193 0.1416 0.4759 0.162 Uiso 1 1 calc R . .
C15 C 0.2151(6) -0.0009(4) 0.50499(15) 0.1184(15) Uani 1 1 d . . .
H15 H 0.1593 -0.0008 0.5352 0.142 Uiso 1 1 calc R . .
C16 C 0.3175(5) -0.0857(3) 0.49655(14) 0.0960(12) Uani 1 1 d . . .
H16 H 0.3305 -0.1455 0.5204 0.115 Uiso 1 1 calc R . .
C17 C 0.4031(4) -0.0844(3) 0.45279(13) 0.0819(10) Uani 1 1 d . . .
H17 H 0.4753 -0.1429 0.4476 0.098 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 0.072(2) 0.313(5) 0.129(3) 0.077(3) -0.0070(17) 0.055(2)
N1 0.0457(18) 0.0636(17) 0.0504(17) 0.000 0.000 0.0040(13)
C1 0.051(2) 0.0508(19) 0.068(2) 0.000 0.000 -0.0037(16)
C2 0.0601(18) 0.0510(14) 0.0570(15) 0.0023(11) 0.0009(12) 0.0140(12)
C3 0.0664(19) 0.0680(17) 0.0619(17) 0.0052(14) 0.0079(14) -0.0003(14)
C4 0.097(2) 0.0614(17) 0.0671(19) -0.0065(14) -0.0024(17) 0.0077(15)
C5 0.091(2) 0.092(2) 0.0636(19) -0.0037(17) 0.0084(18) 0.0340(19)
C6 0.075(2) 0.106(2) 0.072(2) 0.0162(18) 0.0208(17) 0.0099(19)
C7 0.069(2) 0.0690(17) 0.077(2) 0.0100(15) 0.0058(16) -0.0005(14)
C8 0.0519(16) 0.0590(15) 0.0579(15) 0.0076(11) -0.0004(12) 0.0020(11)
C9 0.219(5) 0.0678(19) 0.081(2) 0.0158(16) 0.026(3) 0.050(2)
C10 0.065(2) 0.134(3) 0.086(2) 0.036(2) -0.0221(17) -0.0310(19)
C11 0.057(2) 0.141(3) 0.097(3) 0.032(2) -0.024(2) -0.008(2)
C12 0.073(2) 0.083(2) 0.073(2) 0.0045(16) -0.0326(17) -0.0106(16)
C13 0.145(4) 0.100(3) 0.080(3) 0.0008(19) -0.034(2) 0.021(3)
C14 0.184(5) 0.136(4) 0.085(3) -0.018(3) -0.015(3) 0.063(3)
C15 0.144(4) 0.142(3) 0.069(2) -0.016(2) -0.014(2) 0.021(3)
C16 0.117(3) 0.105(3) 0.066(2) 0.0033(19) -0.023(2) -0.021(2)
C17 0.081(2) 0.085(2) 0.079(2) 0.0022(17) -0.0287(18) -0.0097(16)
_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 C11 1.216(5) . ?
N1 C1 1.469(5) . ?
N1 C8 1.486(3) . ?
N1 C8 1.487(3) 6_556 ?
C1 C2 1.520(3) . ?
C1 C2 1.520(3) 6_556 ?
C1 H1 0.9800 . ?
C2 C3 1.382(4) . ?
C2 C7 1.385(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.355(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.513(4) . ?
C8 C10 1.527(4) . ?
C8 H8 0.9800 . ?
C9 C9 1.363(7) 6_556 ?
C9 H9 0.9300 . ?
C10 C11 1.507(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.485(5) . ?
C12 C13 1.362(5) . ?
C12 C17 1.392(4) . ?
C13 C14 1.390(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.345(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.338(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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 C8 112.65(18) . . ?
C1 N1 C8 112.65(18) . 6_556 ?
C8 N1 C8 106.9(2) . 6_556 ?
N1 C1 C2 111.73(19) . . ?
N1 C1 C2 111.73(19) . 6_556 ?
C2 C1 C2 110.2(3) . 6_556 ?
N1 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
C2 C1 H1 107.7 6_556 . ?
C3 C2 C7 117.6(2) . . ?
C3 C2 C1 123.5(3) . . ?
C7 C2 C1 118.9(3) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 120.9(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N1 C8 C9 105.6(2) . . ?
N1 C8 C10 111.1(2) . . ?
C9 C8 C10 112.7(3) . . ?
N1 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C10 C8 H8 109.1 . . ?
C9 C9 C8 109.82(16) 6_556 . ?
C9 C9 H9 125.1 6_556 . ?
C8 C9 H9 125.1 . . ?
C11 C10 C8 110.9(3) . . ?
C11 C10 H10A 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 C12 119.7(3) . . ?
O1 C11 C10 120.2(4) . . ?
C12 C11 C10 120.0(3) . . ?
C13 C12 C17 117.2(4) . . ?
C13 C12 C11 122.8(3) . . ?
C17 C12 C11 120.0(3) . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 121.3(4) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
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 C2 57.5(3) . . . . ?
C8 N1 C1 C2 178.5(2) 6_556 . . . ?
C8 N1 C1 C2 -178.5(2) . . . 6_556 ?
C8 N1 C1 C2 -57.5(3) 6_556 . . 6_556 ?
N1 C1 C2 C3 47.7(3) . . . . ?
C2 C1 C2 C3 -77.1(4) 6_556 . . . ?
N1 C1 C2 C7 -134.7(3) . . . . ?
C2 C1 C2 C7 100.5(3) 6_556 . . . ?
C7 C2 C3 C4 1.4(4) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C3 C2 C7 C6 -0.8(4) . . . . ?
C1 C2 C7 C6 -178.5(3) . . . . ?
C1 N1 C8 C9 109.9(3) . . . . ?
C8 N1 C8 C9 -14.4(4) 6_556 . . . ?
C1 N1 C8 C10 -127.6(3) . . . . ?
C8 N1 C8 C10 108.1(3) 6_556 . . . ?
N1 C8 C9 C9 9.1(2) . . . 6_556 ?
C10 C8 C9 C9 -112.4(2) . . . 6_556 ?
N1 C8 C10 C11 179.7(3) . . . . ?
C9 C8 C10 C11 -62.0(4) . . . . ?
C8 C10 C11 O1 103.4(4) . . . . ?
C8 C10 C11 C12 -73.1(4) . . . . ?
O1 C11 C12 C13 164.2(4) . . . . ?
C10 C11 C12 C13 -19.2(5) . . . . ?
O1 C11 C12 C17 -15.0(5) . . . . ?
C10 C11 C12 C17 161.5(3) . . . . ?
C17 C12 C13 C14 0.7(5) . . . . ?
C11 C12 C13 C14 -178.6(4) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C13 C14 C15 C16 -1.4(7) . . . . ?
C14 C15 C16 C17 1.9(6) . . . . ?
C15 C16 C17 C12 -1.2(5) . . . . ?
C13 C12 C17 C16 -0.1(4) . . . . ?
C11 C12 C17 C16 179.2(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full 23.29
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max 0.385
_refine_diff_density_min -0.180
_refine_diff_density_rms 0.037