#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:04:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213327.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213327
loop_
_publ_author_name
'Maison, Wolfgang'
'Lützen, Arne'
'Kosten, Marc'
'Schlemminger, Imre'
'Westerhoff, Ole'
'Saak, Wolfgang'
'Martens, Jürgen'
_publ_section_title
;
 Multicomponent synthesis of tripeptides containing pipecolic acid
 derivatives: selective induction of cis- and trans-imide bonds into
 peptide backbones
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1867
_journal_paper_doi               10.1039/b002258f
_journal_year                    2000
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.449(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1496(7)
_cell_length_b                   8.7609(6)
_cell_length_c                   18.8400(12)
_cell_measurement_temperature    193(2)
_cell_volume                     1773.8(2)
_computing_cell_refinement       'IPDS (Stoe, 1997)'
_computing_data_collection       'IPDS (Stoe, 1997)'
_computing_data_reduction        'XRED (Stoe, 1997)'
_computing_molecular_graphics    'XSTEP (Stoe, 1997)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'imaging plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12820
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2558
_reflns_number_total             3465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002258fsup1.cif
_cod_data_source_block           wm242
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7213327
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'
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
N1 N 0.71664(11) 0.35123(13) 0.95368(6) 0.0225(3) Uani 1 1 d
O1 O 0.96939(10) 0.29321(13) 0.97915(6) 0.0326(3) Uani 1 1 d
H1O H 1.049(2) 0.337(3) 0.9900(14) 0.068(7) Uiso 1 1 d
O2 O 0.98425(10) 0.30257(13) 1.10048(6) 0.0348(3) Uani 1 1 d
O3 O 0.82773(10) 0.55410(12) 1.00680(6) 0.0313(3) Uani 1 1 d
C1 C 0.59644(13) 0.28911(16) 0.90973(8) 0.0238(3) Uani 1 1 d
H1 H 0.5559(15) 0.3719(18) 0.8762(10) 0.025(4) Uiso 1 1 d
C2 C 0.51792(13) 0.25874(17) 0.96397(8) 0.0259(3) Uani 1 1 d
H2A H 0.4953(16) 0.3580(19) 0.9810(10) 0.028(4) Uiso 1 1 d
H2B H 0.4384(17) 0.209(2) 0.9405(10) 0.033(4) Uiso 1 1 d
C3 C 0.58598(13) 0.16112(16) 1.02966(8) 0.0241(3) Uani 1 1 d
H3A H 0.6001(14) 0.0549(18) 1.0129(9) 0.022(4) Uiso 1 1 d
H3B H 0.5343(16) 0.1527(18) 1.0643(10) 0.028(4) Uiso 1 1 d
C4 C 0.71663(12) 0.22213(15) 1.07241(7) 0.0221(3) Uani 1 1 d
C5 C 0.78561(12) 0.24705(16) 1.01250(7) 0.0214(3) Uani 1 1 d
H5 H 0.7867(13) 0.1480(17) 0.9885(9) 0.017(3) Uiso 1 1 d
C6 C 0.92367(13) 0.28879(16) 1.03747(8) 0.0253(3) Uani 1 1 d
C7 C 0.74620(13) 0.50076(16) 0.95463(8) 0.0252(3) Uani 1 1 d
C8 C 0.68247(19) 0.6016(2) 0.89126(10) 0.0388(4) Uani 1 1 d
H8A H 0.670(2) 0.555(2) 0.8440(14) 0.059(6) Uiso 1 1 d
H8B H 0.727(2) 0.692(3) 0.8895(15) 0.074(7) Uiso 1 1 d
H8C H 0.599(3) 0.636(3) 0.8934(17) 0.092(9) Uiso 1 1 d
C9 C 0.61436(14) 0.15350(16) 0.86257(7) 0.0251(3) Uani 1 1 d
C10 C 0.72794(15) 0.12719(18) 0.84680(8) 0.0302(3) Uani 1 1 d
H10 H 0.8009(19) 0.195(2) 0.8676(11) 0.045(5) Uiso 1 1 d
C11 C 0.74262(17) 0.00504(19) 0.80263(9) 0.0363(4) Uani 1 1 d
H11 H 0.8238(19) -0.012(2) 0.7941(10) 0.042(5) Uiso 1 1 d
C12 C 0.64269(18) -0.09097(18) 0.77247(9) 0.0373(4) Uani 1 1 d
H12 H 0.6580(17) -0.175(2) 0.7446(11) 0.037(5) Uiso 1 1 d
C13 C 0.52978(17) -0.06457(18) 0.78684(9) 0.0354(4) Uani 1 1 d
H13 H 0.461(2) -0.133(2) 0.7678(12) 0.049(6) Uiso 1 1 d
C14 C 0.51436(15) 0.05669(17) 0.83116(8) 0.0288(3) Uani 1 1 d
H14 H 0.4336(17) 0.0751(19) 0.8412(10) 0.033(4) Uiso 1 1 d
C15 C 0.70328(14) 0.37142(17) 1.11222(8) 0.0268(3) Uani 1 1 d
H15A H 0.6641(17) 0.451(2) 1.0789(10) 0.033(4) Uiso 1 1 d
H15B H 0.7861(18) 0.415(2) 1.1391(11) 0.038(5) Uiso 1 1 d
H15C H 0.6513(17) 0.3552(19) 1.1473(11) 0.034(4) Uiso 1 1 d
C16 C 0.78224(12) 0.09666(16) 1.12616(8) 0.0224(3) Uani 1 1 d
C17 C 0.81664(14) 0.11814(18) 1.20220(8) 0.0282(3) Uani 1 1 d
H17 H 0.8015(16) 0.2148(19) 1.2238(9) 0.028(4) Uiso 1 1 d
C18 C 0.87276(15) 0.0026(2) 1.25006(9) 0.0347(4) Uani 1 1 d
H18 H 0.8934(18) 0.022(2) 1.3045(11) 0.043(5) Uiso 1 1 d
C19 C 0.89553(16) -0.1380(2) 1.22329(9) 0.0364(4) Uani 1 1 d
H19 H 0.9331(18) -0.215(2) 1.2550(12) 0.043(5) Uiso 1 1 d
C20 C 0.86242(17) -0.16261(19) 1.14774(10) 0.0367(4) Uani 1 1 d
H20 H 0.8773(19) -0.262(2) 1.1272(11) 0.048(5) Uiso 1 1 d
C21 C 0.80631(15) -0.04641(17) 1.10003(9) 0.0294(3) Uani 1 1 d
H21 H 0.7819(18) -0.067(2) 1.0467(11) 0.041(5) Uiso 1 1 d
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C1 123.11(12)
C7 N1 C5 120.75(11)
C1 N1 C5 113.84(10)
C6 O1 H1O 112.4(15)
N1 C1 C9 111.86(12)
N1 C1 C2 106.46(11)
C9 C1 C2 115.99(12)
N1 C1 H1 106.3(10)
C9 C1 H1 107.9(10)
C2 C1 H1 107.9(9)
C3 C2 C1 112.80(12)
C3 C2 H2A 110.2(10)
C1 C2 H2A 107.8(10)
C3 C2 H2B 108.2(10)
C1 C2 H2B 112.5(11)
H2A C2 H2B 105.1(14)
C2 C3 C4 114.85(11)
C2 C3 H3A 110.3(9)
C4 C3 H3A 106.0(9)
C2 C3 H3B 109.1(10)
C4 C3 H3B 108.4(10)
H3A C3 H3B 107.9(13)
C15 C4 C16 112.19(11)
C15 C4 C5 111.69(11)
C16 C4 C5 109.89(11)
C15 C4 C3 110.22(12)
C16 C4 C3 108.03(11)
C5 C4 C3 104.49(11)
N1 C5 C6 111.21(11)
N1 C5 C4 111.96(11)
C6 C5 C4 117.80(11)
N1 C5 H5 105.5(9)
C6 C5 H5 102.6(8)
C4 C5 H5 106.4(9)
O2 C6 O1 124.99(14)
O2 C6 C5 125.52(13)
O1 C6 C5 109.21(12)
O3 C7 N1 120.10(13)
O3 C7 C8 120.01(14)
N1 C7 C8 119.87(13)
C7 C8 H8A 114.0(13)
C7 C8 H8B 112.4(17)
H8A C8 H8B 106(2)
C7 C8 H8C 113.4(18)
H8A C8 H8C 105(2)
H8B C8 H8C 105(2)
C10 C9 C14 118.40(14)
C10 C9 C1 121.27(13)
C14 C9 C1 120.25(14)
C11 C10 C9 120.83(15)
C11 C10 H10 118.6(11)
C9 C10 H10 120.5(11)
C12 C11 C10 120.02(17)
C12 C11 H11 121.5(11)
C10 C11 H11 118.5(12)
C13 C12 C11 119.56(16)
C13 C12 H12 123.3(11)
C11 C12 H12 117.0(11)
C12 C13 C14 120.85(15)
C12 C13 H13 120.1(12)
C14 C13 H13 119.1(12)
C13 C14 C9 120.32(16)
C13 C14 H14 120.6(10)
C9 C14 H14 119.1(10)
C4 C15 H15A 112.5(11)
C4 C15 H15B 112.1(10)
H15A C15 H15B 104.7(15)
C4 C15 H15C 110.6(10)
H15A C15 H15C 107.0(15)
H15B C15 H15C 109.7(16)
C17 C16 C21 117.18(13)
C17 C16 C4 122.12(13)
C21 C16 C4 120.67(12)
C18 C17 C16 121.47(14)
C18 C17 H17 117.4(10)
C16 C17 H17 121.1(10)
C19 C18 C17 120.55(15)
C19 C18 H18 120.9(11)
C17 C18 H18 118.5(11)
C18 C19 C20 119.23(15)
C18 C19 H19 120.6(13)
C20 C19 H19 120.2(13)
C19 C20 C21 119.98(16)
C19 C20 H20 120.9(12)
C21 C20 H20 119.1(12)
C20 C21 C16 121.59(15)
C20 C21 H21 118.9(11)
C16 C21 H21 119.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.3498(19)
N1 C1 1.4788(17)
N1 C5 1.4827(17)
O1 C6 1.3293(18)
O1 H1O 0.94(3)
O2 C6 1.2054(18)
O3 C7 1.2389(18)
C1 C9 1.528(2)
C1 C2 1.536(2)
C1 H1 0.988(17)
C2 C3 1.529(2)
C2 H2A 0.983(17)
C2 H2B 0.981(19)
C3 C4 1.5592(19)
C3 H3A 1.009(16)
C3 H3B 0.981(18)
C4 C15 1.535(2)
C4 C16 1.5408(19)
C4 C5 1.5412(19)
C5 C6 1.5292(19)
C5 H5 0.980(15)
C7 C8 1.503(2)
C8 H8A 0.96(2)
C8 H8B 0.94(3)
C8 H8C 0.99(3)
C9 C10 1.395(2)
C9 C14 1.400(2)
C10 C11 1.392(2)
C10 H10 1.00(2)
C11 C12 1.391(2)
C11 H11 0.97(2)
C12 C13 1.376(3)
C12 H12 0.948(19)
C13 C14 1.390(2)
C13 H13 0.96(2)
C14 H14 0.982(18)
C15 H15A 0.959(19)
C15 H15B 1.00(2)
C15 H15C 0.999(19)
C16 C17 1.394(2)
C16 C21 1.398(2)
C17 C18 1.389(2)
C17 H17 0.974(17)
C18 C19 1.380(3)
C18 H18 1.00(2)
C19 C20 1.389(2)
C19 H19 0.92(2)
C20 C21 1.391(2)
C20 H20 0.98(2)
C21 H21 0.98(2)
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
C7 N1 C1 C9 129.03(14)
C5 N1 C1 C9 -68.10(15)
C7 N1 C1 C2 -103.32(15)
C5 N1 C1 C2 59.55(15)
N1 C1 C2 C3 -52.55(15)
C9 C1 C2 C3 72.61(15)
C1 C2 C3 C4 53.43(17)
C2 C3 C4 C15 68.07(16)
C2 C3 C4 C16 -169.04(12)
C2 C3 C4 C5 -52.06(16)
C7 N1 C5 C6 -36.58(18)
C1 N1 C5 C6 160.11(12)
C7 N1 C5 C4 97.52(15)
C1 N1 C5 C4 -65.79(15)
C15 C4 C5 N1 -62.65(14)
C16 C4 C5 N1 172.18(10)
C3 C4 C5 N1 56.49(14)
C15 C4 C5 C6 68.16(16)
C16 C4 C5 C6 -57.01(16)
C3 C4 C5 C6 -172.70(12)
N1 C5 C6 O2 131.96(15)
C4 C5 C6 O2 0.8(2)
N1 C5 C6 O1 -53.96(16)
C4 C5 C6 O1 174.89(12)
C1 N1 C7 O3 158.26(13)
C5 N1 C7 O3 -3.5(2)
C1 N1 C7 C8 -23.4(2)
C5 N1 C7 C8 174.87(14)
N1 C1 C9 C10 -18.58(18)
C2 C1 C9 C10 -140.94(14)
N1 C1 C9 C14 164.55(12)
C2 C1 C9 C14 42.19(18)
C14 C9 C10 C11 -1.8(2)
C1 C9 C10 C11 -178.76(14)
C9 C10 C11 C12 1.2(2)
C10 C11 C12 C13 -0.2(2)
C11 C12 C13 C14 -0.1(2)
C12 C13 C14 C9 -0.6(2)
C10 C9 C14 C13 1.5(2)
C1 C9 C14 C13 178.48(13)
C15 C4 C16 C17 3.86(18)
C5 C4 C16 C17 128.74(14)
C3 C4 C16 C17 -117.83(14)
C15 C4 C16 C21 -178.11(13)
C5 C4 C16 C21 -53.22(16)
C3 C4 C16 C21 60.20(17)
C21 C16 C17 C18 0.2(2)
C4 C16 C17 C18 178.27(14)
C16 C17 C18 C19 -0.3(2)
C17 C18 C19 C20 0.4(3)
C18 C19 C20 C21 -0.4(3)
C19 C20 C21 C16 0.2(3)
C17 C16 C21 C20 -0.1(2)
C4 C16 C21 C20 -178.24(14)
