#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:04:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213325.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_7213325
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            'C24 H35 N3 O6'
_chemical_formula_weight         461.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 103.857(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.179(2)
_cell_length_b                   10.9087(8)
_cell_length_c                   10.7255(9)
_cell_measurement_temperature    193(2)
_cell_volume                     2519.4(4)
_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 0.925
_diffrn_measured_fraction_theta_max 0.925
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9154
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.8872
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          1.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                3461
_reflns_number_total             4539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002258fsup1.cif
_cod_data_source_block           wm267
_cod_original_cell_volume        2519.5(4)
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7213325
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
_atom_site_refinement_flags
O1 O 0.92643(6) 0.61286(14) 1.00581(14) 0.0400(4) Uani 1 1 d .
O2 O 1.02442(7) 0.30480(16) 0.97004(17) 0.0485(4) Uani 1 1 d .
O3 O 0.92316(8) 0.2900(2) 0.9564(2) 0.0696(6) Uani 1 1 d .
O4 O 0.78050(6) 0.55351(12) 1.12787(14) 0.0325(3) Uani 1 1 d .
O5 O 0.62862(6) 0.60761(15) 0.66414(14) 0.0404(4) Uani 1 1 d .
O6 O 0.63746(7) 0.62191(16) 0.88112(16) 0.0433(4) Uani 1 1 d .
N1 N 0.79813(7) 0.67438(14) 0.96809(16) 0.0240(3) Uani 1 1 d .
N2 N 0.90099(7) 0.50877(17) 0.81958(18) 0.0360(4) Uani 1 1 d .
H2N H 0.8718 0.4912 0.7505 0.035(6) Uiso 1 1 calc R
N3 N 0.70507(7) 0.51209(15) 0.79749(17) 0.0304(4) Uani 1 1 d .
H3N H 0.7151 0.4886 0.7266 0.034(6) Uiso 1 1 calc R
C1 C 0.82726(8) 0.65900(17) 0.85911(19) 0.0260(4) Uani 1 1 d .
H1 H 0.7992 0.6058 0.7943 0.031 Uiso 1 1 calc R
C2 C 0.83415(9) 0.78267(19) 0.7926(2) 0.0311(5) Uani 1 1 d .
C3 C 0.87037(11) 0.7650(2) 0.6894(2) 0.0426(6) Uani 1 1 d .
H3A H 0.8481 0.7073 0.6244 0.064 Uiso 1 1 calc R
H3B H 0.9117 0.7322 0.7288 0.064 Uiso 1 1 calc R
H3C H 0.8746 0.8440 0.6488 0.064 Uiso 1 1 calc R
C4 C 0.76845(10) 0.8284(2) 0.7291(2) 0.0374(5) Uani 1 1 d .
H4A H 0.7448 0.8390 0.7948 0.056 Uiso 1 1 calc R
H4B H 0.7475 0.7683 0.6655 0.056 Uiso 1 1 calc R
H4C H 0.7711 0.9071 0.6867 0.056 Uiso 1 1 calc R
C5 C 0.86925(10) 0.87223(19) 0.8941(2) 0.0364(5) Uani 1 1 d .
H5A H 0.9117 0.8407 0.9302 0.044 Uiso 1 1 calc R
H5B H 0.8730 0.9523 0.8532 0.044 Uiso 1 1 calc R
C6 C 0.83639(10) 0.89006(19) 1.0021(2) 0.0355(5) Uani 1 1 d .
H6A H 0.7972 0.9350 0.9676 0.043 Uiso 1 1 calc R
H6B H 0.8628 0.9423 1.0689 0.043 Uiso 1 1 calc R
C7 C 0.82115(8) 0.77160(18) 1.06608(18) 0.0274(5) Uani 1 1 d .
H7 H 0.8597 0.7416 1.1274 0.033 Uiso 1 1 calc R
C8 C 0.77310(10) 0.80353(18) 1.1409(2) 0.0300(5) Uani 1 1 d .
C9 C 0.71274(10) 0.8355(2) 1.0772(2) 0.0401(6) Uani 1 1 d .
H9 H 0.7005 0.8312 0.9862 0.048 Uiso 1 1 calc R
C10 C 0.67043(11) 0.8737(2) 1.1455(3) 0.0510(7) Uani 1 1 d .
H10 H 0.6295 0.8957 1.1008 0.061 Uiso 1 1 calc R
C11 C 0.68727(12) 0.8799(2) 1.2782(3) 0.0529(7) Uani 1 1 d .
H11 H 0.6582 0.9060 1.3248 0.063 Uiso 1 1 calc R
C12 C 0.74673(13) 0.8478(2) 1.3416(3) 0.0469(6) Uani 1 1 d .
H12 H 0.7586 0.8512 1.4327 0.056 Uiso 1 1 calc R
C13 C 0.78970(11) 0.81051(19) 1.2736(2) 0.0376(5) Uani 1 1 d .
H13 H 0.8307 0.7897 1.3186 0.045 Uiso 1 1 calc R
C14 C 0.88924(8) 0.59150(19) 0.9031(2) 0.0287(5) Uani 1 1 d .
C15 C 0.96022(9) 0.4480(2) 0.8402(2) 0.0361(5) Uani 1 1 d .
H15A H 0.9935 0.5075 0.8765 0.043 Uiso 1 1 calc R
H15B H 0.9665 0.4199 0.7565 0.043 Uiso 1 1 calc R
C16 C 0.96579(9) 0.3398(2) 0.9293(2) 0.0354(5) Uani 1 1 d .
C17 C 1.03509(13) 0.1943(3) 1.0478(3) 0.0617(8) Uani 1 1 d .
H17A H 1.0797 0.1766 1.0725 0.093 Uiso 1 1 calc R
H17B H 1.0132 0.1254 0.9982 0.093 Uiso 1 1 calc R
H17C H 1.0196 0.2063 1.1252 0.093 Uiso 1 1 calc R
C18 C 0.77560(8) 0.57109(17) 1.0122(2) 0.0252(4) Uani 1 1 d .
C19 C 0.74270(9) 0.47286(18) 0.9195(2) 0.0317(5) Uani 1 1 d .
H19A H 0.7747 0.4161 0.9027 0.038 Uiso 1 1 calc R
H19B H 0.7159 0.4251 0.9635 0.038 Uiso 1 1 calc R
C20 C 0.65476(9) 0.58407(19) 0.7890(2) 0.0331(5) Uani 1 1 d .
C21 C 0.57407(10) 0.6882(2) 0.6267(2) 0.0407(5) Uani 1 1 d .
C22 C 0.56208(12) 0.6863(3) 0.4812(3) 0.0587(7) Uani 1 1 d .
H22A H 0.5981 0.7203 0.4552 0.088 Uiso 1 1 calc R
H22B H 0.5252 0.7357 0.4441 0.088 Uiso 1 1 calc R
H22C H 0.5552 0.6017 0.4504 0.088 Uiso 1 1 calc R
C23 C 0.51963(10) 0.6369(2) 0.6717(3) 0.0475(6) Uani 1 1 d .
H23A H 0.5290 0.6387 0.7658 0.071 Uiso 1 1 calc R
H23B H 0.5120 0.5521 0.6419 0.071 Uiso 1 1 calc R
H23C H 0.4826 0.6866 0.6368 0.071 Uiso 1 1 calc R
C24 C 0.59045(11) 0.8169(2) 0.6782(3) 0.0547(7) Uani 1 1 d .
H24A H 0.5981 0.8162 0.7721 0.082 Uiso 1 1 calc R
H24B H 0.5559 0.8725 0.6425 0.082 Uiso 1 1 calc R
H24C H 0.6279 0.8450 0.6532 0.082 Uiso 1 1 calc R
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
C16 O2 C17 116.13(19)
C20 O5 C21 120.94(17)
C18 N1 C1 116.63(15)
C18 N1 C7 115.75(17)
C1 N1 C7 119.83(15)
C14 N2 C15 121.55(17)
C20 N3 C19 121.66(18)
N1 C1 C14 110.00(15)
N1 C1 C2 112.09(15)
C14 C1 C2 112.35(15)
C3 C2 C5 109.27(18)
C3 C2 C4 109.14(18)
C5 C2 C4 112.01(17)
C3 C2 C1 110.50(17)
C5 C2 C1 108.51(17)
C4 C2 C1 107.39(16)
C6 C5 C2 111.63(17)
C5 C6 C7 115.38(17)
N1 C7 C8 111.67(15)
N1 C7 C6 110.93(16)
C8 C7 C6 107.44(17)
C13 C8 C9 118.6(2)
C13 C8 C7 120.53(19)
C9 C8 C7 120.71(19)
C10 C9 C8 120.6(2)
C11 C10 C9 120.5(2)
C12 C11 C10 119.1(2)
C11 C12 C13 120.7(3)
C8 C13 C12 120.5(2)
O1 C14 N2 122.02(18)
O1 C14 C1 123.02(18)
N2 C14 C1 114.94(16)
N2 C15 C16 113.07(18)
O3 C16 O2 124.4(2)
O3 C16 C15 124.5(2)
O2 C16 C15 111.11(18)
O4 C18 N1 121.77(18)
O4 C18 C19 117.40(17)
N1 C18 C19 120.83(19)
N3 C19 C18 117.87(16)
O6 C20 N3 124.06(19)
O6 C20 O5 126.72(18)
N3 C20 O5 109.22(18)
O5 C21 C23 111.1(2)
O5 C21 C22 101.70(19)
C23 C21 C22 111.5(2)
O5 C21 C24 110.06(17)
C23 C21 C24 111.4(2)
C22 C21 C24 110.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C14 1.230(2)
O2 C16 1.325(2)
O2 C17 1.453(3)
O3 C16 1.186(3)
O4 C18 1.234(2)
O5 C20 1.350(3)
O5 C21 1.471(3)
O6 C20 1.215(3)
N1 C18 1.363(3)
N1 C1 1.474(3)
N1 C7 1.494(2)
N2 C14 1.340(3)
N2 C15 1.441(2)
N3 C20 1.350(3)
N3 C19 1.438(3)
C1 C14 1.531(3)
C1 C2 1.551(3)
C2 C3 1.528(3)
C2 C5 1.530(3)
C2 C4 1.536(3)
C5 C6 1.522(3)
C6 C7 1.538(3)
C7 C8 1.520(3)
C8 C13 1.384(3)
C8 C9 1.394(3)
C9 C10 1.385(3)
C10 C11 1.384(4)
C11 C12 1.377(4)
C12 C13 1.393(3)
C15 C16 1.505(3)
C18 C19 1.524(3)
C21 C23 1.511(4)
C21 C22 1.519(4)
C21 C24 1.521(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
C18 N1 C1 C14 -70.4(2)
C7 N1 C1 C14 77.5(2)
C18 N1 C1 C2 163.81(16)
C7 N1 C1 C2 -48.2(2)
N1 C1 C2 C3 174.21(16)
C14 C1 C2 C3 49.7(2)
N1 C1 C2 C5 54.4(2)
C14 C1 C2 C5 -70.1(2)
N1 C1 C2 C4 -66.9(2)
C14 C1 C2 C4 168.68(17)
C3 C2 C5 C6 -178.02(17)
C4 C2 C5 C6 60.9(2)
C1 C2 C5 C6 -57.5(2)
C2 C5 C6 C7 53.0(2)
C18 N1 C7 C8 -51.9(2)
C1 N1 C7 C8 159.84(16)
C18 N1 C7 C6 -171.74(16)
C1 N1 C7 C6 40.0(2)
C5 C6 C7 N1 -41.3(2)
C5 C6 C7 C8 -163.61(17)
N1 C7 C8 C13 132.09(19)
C6 C7 C8 C13 -106.1(2)
N1 C7 C8 C9 -52.9(2)
C6 C7 C8 C9 69.0(2)
C13 C8 C9 C10 0.1(3)
C7 C8 C9 C10 -175.0(2)
C8 C9 C10 C11 -0.4(4)
C9 C10 C11 C12 0.1(4)
C10 C11 C12 C13 0.5(4)
C9 C8 C13 C12 0.5(3)
C7 C8 C13 C12 175.6(2)
C11 C12 C13 C8 -0.8(3)
C15 N2 C14 O1 -5.6(3)
C15 N2 C14 C1 172.78(18)
N1 C1 C14 O1 -41.4(3)
C2 C1 C14 O1 84.2(2)
N1 C1 C14 N2 140.18(17)
C2 C1 C14 N2 -94.2(2)
C14 N2 C15 C16 82.5(3)
C17 O2 C16 O3 3.1(4)
C17 O2 C16 C15 -174.8(2)
N2 C15 C16 O3 17.1(3)
N2 C15 C16 O2 -165.00(18)
C1 N1 C18 O4 141.34(17)
C7 N1 C18 O4 -7.9(2)
C1 N1 C18 C19 -39.2(2)
C7 N1 C18 C19 171.55(16)
C20 N3 C19 C18 -62.1(3)
O4 C18 C19 N3 144.35(18)
N1 C18 C19 N3 -35.2(3)
C19 N3 C20 O6 0.5(3)
C19 N3 C20 O5 179.46(17)
C21 O5 C20 O6 1.2(3)
C21 O5 C20 N3 -177.68(17)
C20 O5 C21 C23 -61.1(3)
C20 O5 C21 C22 -179.9(2)
C20 O5 C21 C24 62.7(3)
