#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515989.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_1515989
loop_
_publ_author_name
'Culf, Adrian S.'
'Cuperlović-Culf, Miroslava'
'Léger, Daniel A'
'Decken, Andreas'
_publ_section_title
;
 Small Head-to-Tail Macrocyclic α-Peptoids.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2780
_journal_page_last               2783
_journal_paper_doi               10.1021/ol501102b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C36 H36 N4 O4'
_chemical_formula_sum            'C36 H36 N4 O4'
_chemical_formula_weight         588.69
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.836(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.232(12)
_cell_length_b                   5.508(4)
_cell_length_c                   17.915(12)
_cell_measurement_reflns_used    3350
_cell_measurement_temperature    188(1)
_cell_measurement_theta_max      25.9725
_cell_measurement_theta_min      2.293
_cell_volume                     1543.1(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      188(1)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3201
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.30
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.9532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                2391
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol501102b_si_003.cif
_cod_data_source_block           ac130748
_cod_depositor_comments
'Adding full bibliography for 1515988--1515991.cif.'
_cod_original_cell_volume        1543.0(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1515989
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
C1 C 0.5849(2) 1.0407(6) 0.37827(19) 0.0307(8) Uani 1 1 d
C2 C 0.50463(19) 1.1905(7) 0.3650(2) 0.0304(7) Uani 1 1 d
C3 C 0.41821(18) 1.1191(6) 0.44310(18) 0.0260(7) Uani 1 1 d
C4 C 0.3697(2) 0.9329(6) 0.4708(2) 0.0278(7) Uani 1 1 d
C5 C 0.2884(2) 1.1852(7) 0.5278(2) 0.0352(8) Uani 1 1 d
C6 C 0.4116(2) 0.8159(6) 0.33785(19) 0.0299(7) Uani 1 1 d
C7 C 0.31631(19) 0.8267(6) 0.28219(18) 0.0289(7) Uani 1 1 d
C8 C 0.2812(2) 1.0217(7) 0.2290(2) 0.0363(8) Uani 1 1 d
C9 C 0.1933(2) 1.0308(8) 0.1793(2) 0.0426(9) Uani 1 1 d
C10 C 0.1400(2) 0.8461(8) 0.1833(2) 0.0461(10) Uani 1 1 d
C11 C 0.1742(2) 0.6515(8) 0.2354(3) 0.0469(10) Uani 1 1 d
C12 C 0.2620(2) 0.6420(7) 0.2846(2) 0.0399(9) Uani 1 1 d
C13 C 0.2020(2) 1.0690(7) 0.4778(2) 0.0358(8) Uani 1 1 d
C14 C 0.1492(2) 1.1516(9) 0.3999(3) 0.0533(11) Uani 1 1 d
C15 C 0.0708(3) 1.0401(10) 0.3536(3) 0.0647(14) Uani 1 1 d
C16 C 0.0445(3) 0.8463(10) 0.3855(3) 0.0641(13) Uani 1 1 d
C17 C 0.0962(3) 0.7640(12) 0.4635(4) 0.0783(16) Uani 1 1 d
C18 C 0.1746(3) 0.8735(9) 0.5091(3) 0.0591(13) Uani 1 1 d
N1 N 0.44402(16) 1.0424(5) 0.38481(15) 0.0270(6) Uani 1 1 d
N2 N 0.35955(16) 1.0139(5) 0.54344(15) 0.0299(6) Uani 1 1 d
O1 O 0.59658(15) 0.9720(5) 0.31830(14) 0.0429(7) Uani 1 1 d
O2 O 0.43363(14) 1.3230(4) 0.47328(13) 0.0332(5) Uani 1 1 d
H2A H 0.4768(19) 1.229(6) 0.3075(19) 0.023(8) Uiso 1 1 d
H2B H 0.519(2) 1.349(6) 0.3997(19) 0.027(8) Uiso 1 1 d
H4B H 0.309(2) 0.898(6) 0.424(2) 0.032(9) Uiso 1 1 d
H4A H 0.4002(17) 0.778(6) 0.4831(18) 0.015(7) Uiso 1 1 d
H5A H 0.298(2) 1.328(7) 0.503(2) 0.038(10) Uiso 1 1 d
H5B H 0.295(2) 1.233(7) 0.586(2) 0.048(10) Uiso 1 1 d
H6A H 0.444(2) 0.790(6) 0.302(2) 0.038(9) Uiso 1 1 d
H6B H 0.427(2) 0.681(6) 0.378(2) 0.029(8) Uiso 1 1 d
H8 H 0.322(2) 1.157(8) 0.228(2) 0.058(12) Uiso 1 1 d
H9 H 0.169(2) 1.175(8) 0.147(3) 0.056(12) Uiso 1 1 d
H10 H 0.079(3) 0.852(8) 0.150(3) 0.074(14) Uiso 1 1 d
H11 H 0.137(3) 0.512(8) 0.237(3) 0.064(13) Uiso 1 1 d
H12 H 0.288(3) 0.489(8) 0.321(2) 0.060(12) Uiso 1 1 d
H14 H 0.167(3) 1.302(8) 0.379(3) 0.063(13) Uiso 1 1 d
H15 H 0.034(3) 1.109(8) 0.299(3) 0.081(15) Uiso 1 1 d
H16 H -0.010(3) 0.759(9) 0.349(3) 0.078(15) Uiso 1 1 d
H17 H 0.084(3) 0.605(9) 0.481(3) 0.076(15) Uiso 1 1 d
H18 H 0.209(2) 0.808(7) 0.555(3) 0.053(12) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N2 122.0(3) . 3_676
O1 C1 C2 119.7(3) . .
N2 C1 C2 118.4(3) 3_676 .
N1 C2 C1 110.3(3) . .
N1 C2 H2A 107.0(18) . .
C1 C2 H2A 107.1(18) . .
N1 C2 H2B 109.7(17) . .
C1 C2 H2B 112.6(17) . .
H2A C2 H2B 110(3) . .
O2 C3 N1 122.8(3) . .
O2 C3 C4 121.2(3) . .
N1 C3 C4 116.0(3) . .
N2 C4 C3 111.8(3) . .
N2 C4 H4B 108.4(18) . .
C3 C4 H4B 111.3(18) . .
N2 C4 H4A 108.8(17) . .
C3 C4 H4A 110.0(16) . .
H4B C4 H4A 106(2) . .
N2 C5 C13 111.8(3) . .
N2 C5 H5A 109(2) . .
C13 C5 H5A 113(2) . .
N2 C5 H5B 104(2) . .
C13 C5 H5B 112(2) . .
H5A C5 H5B 107(3) . .
N1 C6 C7 112.7(3) . .
N1 C6 H6A 107(2) . .
C7 C6 H6A 108.8(19) . .
N1 C6 H6B 107.6(19) . .
C7 C6 H6B 113.1(18) . .
H6A C6 H6B 107(3) . .
C8 C7 C12 118.6(3) . .
C8 C7 C6 121.1(3) . .
C12 C7 C6 120.3(3) . .
C7 C8 C9 120.4(4) . .
C7 C8 H8 118(2) . .
C9 C8 H8 122(2) . .
C10 C9 C8 120.1(4) . .
C10 C9 H9 120(2) . .
C8 C9 H9 120(2) . .
C11 C10 C9 119.9(4) . .
C11 C10 H10 119(3) . .
C9 C10 H10 121(3) . .
C10 C11 C12 119.8(4) . .
C10 C11 H11 121(2) . .
C12 C11 H11 119(2) . .
C7 C12 C11 121.1(4) . .
C7 C12 H12 119(2) . .
C11 C12 H12 119(2) . .
C14 C13 C18 118.2(4) . .
C14 C13 C5 121.5(4) . .
C18 C13 C5 120.3(3) . .
C13 C14 C15 121.1(4) . .
C13 C14 H14 118(2) . .
C15 C14 H14 120(2) . .
C16 C15 C14 120.0(4) . .
C16 C15 H15 121(3) . .
C14 C15 H15 118(3) . .
C15 C16 C17 119.4(4) . .
C15 C16 H16 118(3) . .
C17 C16 H16 122(3) . .
C16 C17 C18 120.5(5) . .
C16 C17 H17 119(3) . .
C18 C17 H17 119(3) . .
C13 C18 C17 120.8(4) . .
C13 C18 H18 119(3) . .
C17 C18 H18 119(3) . .
C3 N1 C6 122.1(3) . .
C3 N1 C2 120.2(3) . .
C6 N1 C2 117.7(3) . .
C1 N2 C4 124.0(3) 3_676 .
C1 N2 C5 120.4(3) 3_676 .
C4 N2 C5 115.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.233(4) .
C1 N2 1.359(4) 3_676
C1 C2 1.541(5) .
C2 N1 1.481(4) .
C2 H2A 0.96(3) .
C2 H2B 1.04(3) .
C3 O2 1.226(4) .
C3 N1 1.363(4) .
C3 C4 1.531(5) .
C4 N2 1.454(4) .
C4 H4B 1.04(3) .
C4 H4A 0.98(3) .
C5 N2 1.478(4) .
C5 C13 1.519(5) .
C5 H5A 0.95(4) .
C5 H5B 1.03(4) .
C6 N1 1.477(4) .
C6 C7 1.522(4) .
C6 H6A 1.02(4) .
C6 H6B 0.99(3) .
C7 C8 1.394(5) .
C7 C12 1.395(5) .
C8 C9 1.399(5) .
C8 H8 1.03(4) .
C9 C10 1.393(6) .
C9 H9 0.97(4) .
C10 C11 1.380(6) .
C10 H10 0.97(4) .
C11 C12 1.396(5) .
C11 H11 1.00(4) .
C12 H12 1.04(4) .
C13 C14 1.384(5) .
C13 C18 1.386(6) .
C14 C15 1.396(6) .
C14 H14 1.01(4) .
C15 C16 1.375(7) .
C15 H15 0.99(5) .
C16 C17 1.379(7) .
C16 H16 1.02(5) .
C17 C18 1.389(6) .
C17 H17 0.98(5) .
C18 H18 0.87(4) .
N2 C1 1.359(4) 3_676
