#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:59:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180117 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/15/7101595.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_7101595
loop_
_publ_author_name
'M. Khurram N. Qureshi'
'Martin D. Smith'
_publ_section_title
;
Parallel sheet structure in cyclopropane γ-peptides stabilized by
C--H...O hydrogen bonds
;
_journal_issue                   48
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b611882h
_journal_year                    2006
_chemical_absolute_configuration
;
1568 Friedel pairs were averaged for the refinement. The absolute
structure was assigned from the KNOWN configuration of the starting
material.
;
_chemical_formula_moiety         'C18 H27 N5 O4'
_chemical_formula_sum            'C18 H27 N5 O4'
_chemical_formula_weight         377.45
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.793(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.80230(10)
_cell_length_b                   8.6693(2)
_cell_length_c                   24.1050(5)
_cell_measurement_reflns_used    10973
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      1.02
_cell_volume                     1001.36(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8057
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0447
_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)+(0.0485P)²+0.3719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2022
_reflns_number_total             2142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b611882h.txt
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7101595
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4298(11) 0.2727(9) 0.02412(14) 0.135(3) Uani 1 1 d . . .
N2 N 0.5463(7) 0.2639(5) 0.06580(11) 0.0705(10) Uani 1 1 d . . .
N3 N 0.6948(7) 0.2528(5) 0.10751(11) 0.0704(10) Uani 1 1 d . . .
N4 N 0.6252(4) 0.2165(3) 0.35521(8) 0.0318(5) Uani 1 1 d . . .
H4N H 0.4448 0.2240 0.3500 0.038 Uiso 1 1 calc R . .
N5 N 0.7432(4) 0.3430(3) 0.59899(8) 0.0340(5) Uani 1 1 d . A .
H5N H 0.9204 0.3410 0.5935 0.041 Uiso 1 1 calc R . .
O1 O 1.0349(4) 0.1795(3) 0.31762(8) 0.0438(5) Uani 1 1 d . . .
O2 O 0.3051(3) 0.3540(3) 0.55947(7) 0.0408(5) Uani 1 1 d . . .
O3 O 1.1387(6) 0.1028(4) 0.79901(10) 0.0709(8) Uani 1 1 d . A .
C1 C 0.7772(5) 0.1844(3) 0.31267(10) 0.0320(6) Uani 1 1 d . . .
C2 C 0.6216(5) 0.1567(4) 0.25810(10) 0.0350(6) Uani 1 1 d . . .
H2 H 0.4153 0.1577 0.2578 0.042 Uiso 1 1 calc R . .
C3 C 0.7493(7) 0.0458(4) 0.21841(12) 0.0435(7) Uani 1 1 d . . .
H3A H 0.9281 -0.0020 0.2304 0.052 Uiso 1 1 calc R . .
H3B H 0.6224 -0.0201 0.1954 0.052 Uiso 1 1 calc R . .
C4' C 0.5570(5) 0.2987(3) 0.45048(10) 0.0294(5) Uani 1 1 d . . .
H4' H 0.3946 0.2319 0.4565 0.035 Uiso 1 1 calc R . .
C4 C 0.7479(6) 0.2135(3) 0.20624(11) 0.0366(6) Uiso 1 1 d . . .
H4 H 0.9303 0.2662 0.2122 0.044 Uiso 1 1 calc R . .
C5 C 0.5585(6) 0.2763(4) 0.16047(11) 0.0473(7) Uani 1 1 d . . .
H5A H 0.5256 0.3865 0.1665 0.057 Uiso 1 1 calc R . .
H5B H 0.3786 0.2227 0.1592 0.057 Uiso 1 1 calc R . .
C1' C 0.5597(5) 0.3593(3) 0.55542(10) 0.0298(5) Uani 1 1 d . . .
C2' C 0.6826(5) 0.3839(3) 0.50107(9) 0.0310(6) Uani 1 1 d . . .
H2' H 0.8868 0.4012 0.5025 0.037 Uiso 1 1 calc R . .
C3' C 0.5110(6) 0.4683(4) 0.45558(11) 0.0375(6) Uani 1 1 d . . .
H3'A H 0.3241 0.5034 0.4638 0.045 Uiso 1 1 calc R . .
H3'B H 0.6098 0.5366 0.4311 0.045 Uiso 1 1 calc R . .
C5' C 0.7589(5) 0.2392(4) 0.41086(10) 0.0329(6) Uani 1 1 d . . .
H5'A H 0.9131 0.3127 0.4089 0.039 Uiso 1 1 calc R . .
H5'B H 0.8369 0.1410 0.4247 0.039 Uiso 1 1 calc R . .
C1" C 0.9123(6) 0.1633(4) 0.79481(11) 0.0443(7) Uani 1 1 d . . .
C2"A C 0.7283(6) 0.1672(4) 0.74367(12) 0.0432(4) Uiso 0.549(9) 1 d PD A 1
H2"A H 0.5240 0.1697 0.7470 0.052 Uiso 0.549(9) 1 calc PR A 1
C3"A C 0.8491(18) 0.0605(7) 0.6962(2) 0.0432(4) Uiso 0.549(9) 1 d PD A 1
H3"A H 1.0307 0.0109 0.7043 0.052 Uiso 0.549(9) 1 calc PR A 1
H3"B H 0.7157 0.0006 0.6724 0.052 Uiso 0.549(9) 1 calc PR A 1
C4"A C 0.8424(6) 0.2285(4) 0.69105(12) 0.0432(4) Uiso 0.549(9) 1 d PD A 1
H4"A H 1.0300 0.2745 0.6982 0.052 Uiso 0.549(9) 1 calc PR A 1
C2"B C 0.7283(6) 0.1672(4) 0.74367(12) 0.0432(4) Uiso 0.451(9) 1 d PD A 2
H2"B H 0.5439 0.2124 0.7502 0.052 Uiso 0.451(9) 1 calc PR A 2
C3"B C 0.714(2) 0.0649(8) 0.6965(3) 0.0432(4) Uiso 0.451(9) 1 d PD A 2
H3"C H 0.5297 0.0458 0.6777 0.052 Uiso 0.451(9) 1 calc PR A 2
H3"D H 0.8408 -0.0236 0.6975 0.052 Uiso 0.451(9) 1 calc PR A 2
C4"B C 0.8424(6) 0.2285(4) 0.69105(12) 0.0432(4) Uiso 0.451(9) 1 d PD A 2
H4"B H 1.0469 0.2385 0.6892 0.052 Uiso 0.451(9) 1 calc PR A 2
C5" C 0.6569(6) 0.3285(4) 0.65552(10) 0.0421(7) Uani 1 1 d . . .
H5"A H 0.4672 0.2864 0.6542 0.051 Uiso 1 1 calc R A 1
H5"B H 0.6521 0.4313 0.6723 0.051 Uiso 1 1 calc R A 1
O4 O 0.8011(4) 0.2421(3) 0.83559(8) 0.0504(6) Uani 1 1 d . A .
C6" C 0.9617(7) 0.2488(5) 0.88932(12) 0.0542(9) Uani 1 1 d . . .
H6" H 1.1638 0.2492 0.8834 0.065 Uiso 1 1 calc R A .
C7" C 0.8917(11) 0.1104(5) 0.92272(16) 0.0751(13) Uani 1 1 d . A .
H7"A H 0.9397 0.0175 0.9030 0.113 Uiso 1 1 calc R . .
H7"B H 0.6935 0.1102 0.9283 0.113 Uiso 1 1 calc R . .
H7"C H 0.9966 0.1136 0.9585 0.113 Uiso 1 1 calc R . .
C8" C 0.8810(11) 0.3988(6) 0.91489(16) 0.0770(13) Uani 1 1 d . A .
H8"A H 0.9316 0.4835 0.8913 0.115 Uiso 1 1 calc R . .
H8"B H 0.9780 0.4097 0.9513 0.115 Uiso 1 1 calc R . .
H8"C H 0.6811 0.4002 0.9187 0.115 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
N1 N2 N3 173.3(4)
N2 N3 C5 116.0(3)
C1 N4 C5' 120.46(19)
C1 N4 H4N 119.8
C5' N4 H4N 119.8
C1' N5 C5" 122.2(2)
C1' N5 H5N 118.9
C5" N5 H5N 118.9
O1 C1 N4 122.1(2)
O1 C1 C2 121.4(2)
N4 C1 C2 116.6(2)
C1 C2 C4 118.3(2)
C1 C2 C3 117.4(2)
C4 C2 C3 58.79(19)
C1 C2 H2 116.6
C4 C2 H2 116.6
C3 C2 H2 116.6
C4 C3 C2 60.4(2)
C4 C3 H3A 117.7
C2 C3 H3A 117.7
C4 C3 H3B 117.7
C2 C3 H3B 117.7
H3A C3 H3B 114.9
C3' C4' C5' 119.8(2)
C3' C4' C2' 60.50(18)
C5' C4' C2' 116.2(2)
C3' C4' H4' 116.2
C5' C4' H4' 116.2
C2' C4' H4' 116.2
C3 C4 C5 120.0(3)
C3 C4 C2 60.8(2)
C5 C4 C2 118.4(2)
C3 C4 H4 115.5
C5 C4 H4 115.5
C2 C4 H4 115.5
C4 C5 N3 107.7(3)
C4 C5 H5A 110.2
N3 C5 H5A 110.2
C4 C5 H5B 110.2
N3 C5 H5B 110.2
H5A C5 H5B 108.5
O2 C1' N5 122.7(2)
O2 C1' C2' 121.9(2)
N5 C1' C2' 115.4(2)
C1' C2' C3' 118.6(2)
C1' C2' C4' 118.6(2)
C3' C2' C4' 58.97(17)
C1' C2' H2' 116.2
C3' C2' H2' 116.2
C4' C2' H2' 116.2
C4' C3' C2' 60.53(18)
C4' C3' H3'A 117.7
C2' C3' H3'A 117.7
C4' C3' H3'B 117.7
C2' C3' H3'B 117.7
H3'A C3' H3'B 114.8
N4 C5' C4' 111.60(19)
N4 C5' H5'A 109.3
C4' C5' H5'A 109.3
N4 C5' H5'B 109.3
C4' C5' H5'B 109.3
H5'A C5' H5'B 108.0
O3 C1" O4 124.2(3)
O3 C1" C2"A 124.8(3)
O4 C1" C2"A 111.0(3)
C1" C2"A C4"A 118.8(3)
C1" C2"A C3"A 111.0(3)
C4"A C2"A C3"A 55.8(3)
C1" C2"A H2"A 118.5
C4"A C2"A H2"A 118.5
C3"A C2"A H2"A 118.5
C4"A C3"A C2"A 58.7(3)
C4"A C3"A H3"A 117.9
C2"A C3"A H3"A 117.9
C4"A C3"A H3"B 117.9
C2"A C3"A H3"B 117.9
H3"A C3"A H3"B 115.1
C3"A C4"A C5" 130.1(4)
C3"A C4"A C2"A 65.5(3)
C5" C4"A C2"A 117.1(3)
C3"A C4"A H4"A 111.8
C5" C4"A H4"A 111.8
C2"A C4"A H4"A 111.8
H3"C C3"B H3"D 114.8
N5 C5" C4"A 113.3(2)
N5 C5" H5"A 108.9
C4"A C5" H5"A 108.9
N5 C5" H5"B 108.9
C4"A C5" H5"B 108.9
H5"A C5" H5"B 107.7
C1" O4 C6" 117.2(3)
O4 C6" C7" 108.7(3)
O4 C6" C8" 105.2(3)
C7" C6" C8" 113.6(3)
O4 C6" H6" 109.7
C7" C6" H6" 109.7
C8" C6" H6" 109.7
C6" C7" H7"A 109.5
C6" C7" H7"B 109.5
H7"A C7" H7"B 109.5
C6" C7" H7"C 109.5
H7"A C7" H7"C 109.5
H7"B C7" H7"C 109.5
C6" C8" H8"A 109.5
C6" C8" H8"B 109.5
H8"A C8" H8"B 109.5
C6" C8" H8"C 109.5
H8"A C8" H8"C 109.5
H8"B C8" H8"C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.120(5)
N2 N3 1.198(4)
N3 C5 1.487(4)
N4 C1 1.327(3)
N4 C5' 1.462(3)
N4 H4N 0.8700
N5 C1' 1.333(3)
N5 C5" 1.456(3)
N5 H5N 0.8700
O1 C1 1.236(3)
O2 C1' 1.234(3)
O3 C1" 1.205(4)
C1 C2 1.489(3)
C2 C4 1.508(4)
C2 C3 1.514(4)
C2 H2 0.9900
C3 C4 1.483(5)
C3 H3A 0.9800
C3 H3B 0.9800
C4' C3' 1.492(4)
C4' C5' 1.497(3)
C4' C2' 1.516(3)
C4' H4' 0.9900
C4 C5 1.486(4)
C4 H4 0.9900
C5 H5A 0.9800
C5 H5B 0.9800
C1' C2' 1.487(3)
C2' C3' 1.516(4)
C2' H2' 0.9900
C3' H3'A 0.9800
C3' H3'B 0.9800
C5' H5'A 0.9800
C5' H5'B 0.9800
C1" O4 1.337(4)
C1" C2"A 1.469(4)
C2"A C4"A 1.511(4)
C2"A C3"A 1.609(7)
C2"A H2"A 0.9900
C3"A C4"A 1.462(7)
C3"A H3"A 0.9800
C3"A H3"B 0.9800
C4"A C5" 1.475(4)
C4"A H4"A 0.9900
C3"B H3"C 0.9800
C3"B H3"D 0.9800
C5" H5"A 0.9800
C5" H5"B 0.9800
O4 C6" 1.464(3)
C6" C7" 1.496(6)
C6" C8" 1.501(6)
C6" H6" 0.9900
C7" H7"A 0.9700
C7" H7"B 0.9700
C7" H7"C 0.9700
C8" H8"A 0.9700
C8" H8"B 0.9700
C8" H8"C 0.9700
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
N1 N2 N3 C5 175(5)
C5' N4 C1 O1 -3.3(4)
C5' N4 C1 C2 177.5(3)
O1 C1 C2 C4 -35.8(4)
N4 C1 C2 C4 143.4(3)
O1 C1 C2 C3 31.7(4)
N4 C1 C2 C3 -149.2(3)
C1 C2 C3 C4 -108.0(3)
C2 C3 C4 C5 -107.8(3)
C1 C2 C4 C3 106.6(3)
C1 C2 C4 C5 -142.9(3)
C3 C2 C4 C5 110.5(3)
C3 C4 C5 N3 -82.1(4)
C2 C4 C5 N3 -152.9(3)
N2 N3 C5 C4 163.4(4)
C5" N5 C1' O2 -4.4(4)
C5" N5 C1' C2' 175.8(3)
O2 C1' C2' C3' 25.8(4)
N5 C1' C2' C3' -154.4(2)
O2 C1' C2' C4' -42.4(4)
N5 C1' C2' C4' 137.4(2)
C3' C4' C2' C1' 107.9(3)
C5' C4' C2' C1' -141.0(2)
C5' C4' C2' C3' 111.1(3)
C5' C4' C3' C2' -105.0(2)
C1' C2' C3' C4' -108.0(3)
C1 N4 C5' C4' 170.8(2)
C3' C4' C5' N4 -87.6(3)
C2' C4' C5' N4 -157.1(2)
O3 C1" C2"A C4"A -53.7(5)
O4 C1" C2"A C4"A 123.3(3)
O3 C1" C2"A C3"A 7.8(5)
O4 C1" C2"A C3"A -175.1(3)
C1" C2"A C3"A C4"A -111.2(3)
C2"A C3"A C4"A C5" -105.7(4)
C1" C2"A C4"A C3"A 96.9(5)
C1" C2"A C4"A C5" -138.9(3)
C3"A C2"A C4"A C5" 124.2(5)
C1' N5 C5" C4"A 146.9(3)
C3"A C4"A C5" N5 -82.2(5)
C2"A C4"A C5" N5 -161.9(3)
O3 C1" O4 C6" -2.8(5)
C2"A C1" O4 C6" -179.9(3)
C1" O4 C6" C7" -86.9(4)
C1" O4 C6" C8" 151.1(3)
