#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/88/1508894.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1508894
loop_
_publ_author_name
'Izzo, Irene'
'Ianniello, Graziella'
'De Cola, Chiara'
'Nardone, Brunello'
'Erra, Loredana'
'Vaughan, Gavin'
'Tedesco, Consiglia'
'De Riccardis, Francesco'
_publ_section_title
;
 Structural effects of proline substitution and metal binding on hexameric
 cyclic peptoids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              598
_journal_page_last               601
_journal_paper_doi               10.1021/ol3034143
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C30 H54 N6 O12'
_chemical_formula_sum            'C30 H54 N6 O12'
_chemical_formula_weight         690.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.636(6)
_cell_angle_beta                 101.488(12)
_cell_angle_gamma                104.239(13)
_cell_formula_units_Z            1
_cell_length_a                   8.3584(35)
_cell_length_b                   9.1756(36)
_cell_length_c                   11.6234(42)
_cell_measurement_reflns_used    5398
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3430
_cell_measurement_theta_min      1.836
_cell_volume                     824.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.900
_diffrn_measured_fraction_theta_max 0.900
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8858
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0460
_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)+(0.0670P)²+0.0333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                3091
_reflns_number_total             3734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3034143_si_002.cif
_cod_data_source_block           21
_cod_database_code               1508894
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.60699(13) 0.24150(13) 1.02463(10) 0.0177(3) Uani 1 1 d .
C2 C 0.48396(16) 0.25420(16) 0.93757(12) 0.0177(3) Uani 1 1 d .
C3 C 0.47652(16) 0.17959(16) 0.81045(12) 0.0178(3) Uani 1 1 d .
H3A H 0.5897 0.2169 0.7944 0.021 Uiso 1 1 calc R
H3B H 0.4503 0.0664 0.8018 0.021 Uiso 1 1 calc R
N4 N 0.35135(13) 0.21169(13) 0.72338(10) 0.0179(3) Uani 1 1 d .
C5 C 0.37041(16) 0.34877(16) 0.69695(12) 0.0183(3) Uani 1 1 d .
C6 C 0.54074(16) 0.46744(16) 0.75590(12) 0.0188(3) Uani 1 1 d .
H6A H 0.5649 0.4775 0.8442 0.023 Uiso 1 1 calc R
H6B H 0.6311 0.4311 0.7272 0.023 Uiso 1 1 calc R
N7 N 0.54599(14) 0.61505(13) 0.73061(10) 0.0187(3) Uani 1 1 d .
C8 C 0.47665(16) 0.71200(16) 0.78625(12) 0.0181(3) Uani 1 1 d .
C9 C 0.64180(17) 0.34532(17) 1.13943(12) 0.0198(3) Uani 1 1 d .
H9A H 0.6318 0.4470 1.1265 0.024 Uiso 1 1 calc R
H9B H 0.7606 0.3601 1.1843 0.024 Uiso 1 1 calc R
C10 C 0.71005(17) 0.13889(17) 1.00856(13) 0.0206(3) Uani 1 1 d .
H10A H 0.6504 0.0561 0.9352 0.025 Uiso 1 1 calc R
H10B H 0.7223 0.0897 1.0781 0.025 Uiso 1 1 calc R
C11 C 0.88325(18) 0.21690(18) 0.99721(13) 0.0239(3) Uani 1 1 d .
H11A H 0.9465 0.2974 1.0713 0.029 Uiso 1 1 calc R
H11B H 0.9480 0.1408 0.9865 0.029 Uiso 1 1 calc R
O12 O 0.86611(12) 0.28343(13) 0.89845(9) 0.0250(3) Uani 1 1 d .
C13 C 1.02435(18) 0.3584(2) 0.88205(15) 0.0321(4) Uani 1 1 d .
H13A H 1.0070 0.4033 0.8114 0.048 Uiso 1 1 calc R
H13B H 1.0890 0.2838 0.8695 0.048 Uiso 1 1 calc R
H13C H 1.0880 0.4405 0.9537 0.048 Uiso 1 1 calc R
O14 O 0.38956(12) 0.32924(12) 0.95985(9) 0.0214(2) Uani 1 1 d .
C15 C 0.19349(17) 0.09099(16) 0.67090(12) 0.0201(3) Uani 1 1 d .
H15A H 0.1063 0.1356 0.6320 0.024 Uiso 1 1 calc R
H15B H 0.1529 0.0467 0.7355 0.024 Uiso 1 1 calc R
C16 C 0.21287(18) -0.03404(17) 0.58002(13) 0.0222(3) Uani 1 1 d .
H16A H 0.3045 -0.0754 0.6168 0.027 Uiso 1 1 calc R
H16B H 0.1053 -0.1194 0.5514 0.027 Uiso 1 1 calc R
O17 O 0.25328(13) 0.02578(12) 0.48371(9) 0.0254(3) Uani 1 1 d .
C18 C 0.2835(2) -0.08283(19) 0.39791(14) 0.0308(4) Uani 1 1 d .
H18A H 0.3111 -0.0361 0.3318 0.046 Uiso 1 1 calc R
H18B H 0.1813 -0.1716 0.3663 0.046 Uiso 1 1 calc R
H18C H 0.3792 -0.1172 0.4353 0.046 Uiso 1 1 calc R
O19 O 0.26133(12) 0.38051(12) 0.62898(9) 0.0228(2) Uani 1 1 d .
C20 C 0.63177(17) 0.66195(17) 0.64161(13) 0.0210(3) Uani 1 1 d .
H20A H 0.5792 0.7343 0.6049 0.025 Uiso 1 1 calc R
H20B H 0.6143 0.5700 0.5770 0.025 Uiso 1 1 calc R
C21 C 0.81841(17) 0.73789(17) 0.69033(13) 0.0234(3) Uani 1 1 d .
H21A H 0.8626 0.7898 0.6301 0.028 Uiso 1 1 calc R
H21B H 0.8370 0.8183 0.7639 0.028 Uiso 1 1 calc R
O22 O 0.91136(12) 0.63468(13) 0.71848(9) 0.0262(3) Uani 1 1 d .
C23 C 0.9363(2) 0.5490(2) 0.61599(14) 0.0291(4) Uani 1 1 d .
H23A H 1.0011 0.4785 0.6397 0.044 Uiso 1 1 calc R
H23B H 0.9998 0.6191 0.5748 0.044 Uiso 1 1 calc R
H23C H 0.8255 0.4892 0.5615 0.044 Uiso 1 1 calc R
O24 O 0.49922(13) 0.84341(12) 0.77347(9) 0.0242(2) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C9 116.01(11) . .
C2 N1 C10 124.63(11) . .
C9 N1 C10 119.27(11) . .
O14 C2 N1 121.17(13) . .
O14 C2 C3 121.86(12) . .
N1 C2 C3 116.85(11) . .
N4 C3 C2 112.58(11) . .
N4 C3 H3A 109.1 . .
C2 C3 H3A 109.1 . .
N4 C3 H3B 109.1 . .
C2 C3 H3B 109.1 . .
H3A C3 H3B 107.8 . .
C5 N4 C3 122.81(11) . .
C5 N4 C15 120.03(12) . .
C3 N4 C15 116.96(12) . .
O19 C5 N4 123.59(12) . .
O19 C5 C6 120.30(13) . .
N4 C5 C6 116.11(12) . .
N7 C6 C5 112.54(11) . .
N7 C6 H6A 109.1 . .
C5 C6 H6A 109.1 . .
N7 C6 H6B 109.1 . .
C5 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
C8 N7 C6 123.06(12) . .
C8 N7 C20 118.29(12) . .
C6 N7 C20 118.65(11) . .
O24 C8 N7 121.84(13) . .
O24 C8 C9 119.02(12) . 2_667
N7 C8 C9 119.02(13) . 2_667
N1 C9 C8 112.64(11) . 2_667
N1 C9 H9A 109.1 . .
C8 C9 H9A 109.1 2_667 .
N1 C9 H9B 109.1 . .
C8 C9 H9B 109.1 2_667 .
H9A C9 H9B 107.8 . .
N1 C10 C11 113.63(12) . .
N1 C10 H10A 108.8 . .
C11 C10 H10A 108.8 . .
N1 C10 H10B 108.8 . .
C11 C10 H10B 108.8 . .
H10A C10 H10B 107.7 . .
O12 C11 C10 108.82(11) . .
O12 C11 H11A 109.9 . .
C10 C11 H11A 109.9 . .
O12 C11 H11B 109.9 . .
C10 C11 H11B 109.9 . .
H11A C11 H11B 108.3 . .
C11 O12 C13 111.90(11) . .
O12 C13 H13A 109.5 . .
O12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N4 C15 C16 111.99(11) . .
N4 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
N4 C15 H15B 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
O17 C16 C15 108.91(12) . .
O17 C16 H16A 109.9 . .
C15 C16 H16A 109.9 . .
O17 C16 H16B 109.9 . .
C15 C16 H16B 109.9 . .
H16A C16 H16B 108.3 . .
C16 O17 C18 112.18(12) . .
O17 C18 H18A 109.5 . .
O17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N7 C20 C21 113.84(12) . .
N7 C20 H20A 108.8 . .
C21 C20 H20A 108.8 . .
N7 C20 H20B 108.8 . .
C21 C20 H20B 108.8 . .
H20A C20 H20B 107.7 . .
O22 C21 C20 113.37(13) . .
O22 C21 H21A 108.9 . .
C20 C21 H21A 108.9 . .
O22 C21 H21B 108.9 . .
C20 C21 H21B 108.9 . .
H21A C21 H21B 107.7 . .
C23 O22 C21 112.20(12) . .
O22 C23 H23A 109.5 . .
O22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
O22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.3338(18) .
N1 C9 1.4339(17) .
N1 C10 1.4380(17) .
C2 O14 1.2052(16) .
C2 C3 1.5032(19) .
C3 N4 1.4266(18) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
N4 C5 1.3237(19) .
N4 C15 1.4402(17) .
C5 O19 1.2087(17) .
C5 C6 1.5104(19) .
C6 N7 1.4255(18) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
N7 C8 1.3251(17) .
N7 C20 1.4360(18) .
C8 O24 1.2127(18) .
C8 C9 1.4966(19) 2_667
C9 C8 1.4966(19) 2_667
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.491(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 O12 1.3868(19) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
O12 C13 1.3984(18) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C15 C16 1.4873(19) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 O17 1.3906(18) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
O17 C18 1.3937(17) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C20 C21 1.490(2) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 O22 1.4042(19) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
O22 C23 1.3952(17) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
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_4
C9 N1 C2 O14 -12.16(19) .
C10 N1 C2 O14 171.46(13) .
C9 N1 C2 C3 163.92(12) .
C10 N1 C2 C3 -12.45(19) .
O14 C2 C3 N4 1.55(19) .
N1 C2 C3 N4 -174.50(12) .
C2 C3 N4 C5 72.43(16) .
C2 C3 N4 C15 -102.51(14) .
C3 N4 C5 O19 -175.28(12) .
C15 N4 C5 O19 -0.50(19) .
C3 N4 C5 C6 5.53(18) .
C15 N4 C5 C6 -179.69(11) .
O19 C5 C6 N7 5.55(18) .
N4 C5 C6 N7 -175.23(11) .
C5 C6 N7 C8 78.37(16) .
C5 C6 N7 C20 -102.28(14) .
C6 N7 C8 O24 171.41(12) .
C20 N7 C8 O24 -7.95(19) .
C6 N7 C8 C9 -12.61(19) 2_667
C20 N7 C8 C9 168.03(12) 2_667
C2 N1 C9 C8 83.54(16) 2_667
C10 N1 C9 C8 -99.88(14) 2_667
C2 N1 C10 C11 101.18(15) .
C9 N1 C10 C11 -75.09(16) .
N1 C10 C11 O12 -59.62(16) .
C10 C11 O12 C13 -179.74(12) .
C5 N4 C15 C16 109.29(14) .
C3 N4 C15 C16 -75.63(16) .
N4 C15 C16 O17 -64.79(16) .
C15 C16 O17 C18 176.43(12) .
C8 N7 C20 C21 92.78(15) .
C6 N7 C20 C21 -86.60(15) .
N7 C20 C21 O22 72.77(15) .
C20 C21 O22 C23 77.49(15) .
