#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/71/2017145.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2017145
loop_
_publ_author_name
'Görbitz, Carl Henrik'
'Rissanen, Kari'
'Valkonen, Arto'
'Husabø, Åsmund'
_publ_section_title
;
 Molecular aggregation in selected crystalline 1:1 complexes of
 hydrophobic <small>D</small>- and <small>L</small>-amino acids. IV.
 The <small>L</small>-phenylalanine series
;
_journal_coeditor_code           SK3316
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o267
_journal_page_last               o272
_journal_paper_doi               10.1107/S0108270109014309
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H11 N O2, C6 H13 N O2'
_chemical_formula_moiety         'C9 H11 N O2, C6 H13 N O2'
_chemical_formula_sum            'C15 H24 N2 O4'
_chemical_formula_weight         296.36
_chemical_name_systematic
;
L-Phenylalanine--D-leucine (1/1)
;
_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                 110.3720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1861(5)
_cell_length_b                   29.698(3)
_cell_length_c                   5.4158(5)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.74
_cell_volume                     781.95(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008a)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008a)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008a)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008a)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD diffractometer'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5° ω rotation'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7778
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008b)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1411
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0360
_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)+(0.0438P)²+0.1739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                1269
_reflns_number_total             1411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sk3316.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2017145
_cod_database_fobs_code          2017145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.1937(4) 0.65841(9) 0.6354(4) 0.0413(7) Uani d . 1 . .
O O2A 0.6475(4) 0.65012(8) 0.7847(4) 0.0356(5) Uani d . 1 . .
N N1A 0.2052(5) 0.67014(10) 1.1385(5) 0.0303(6) Uani d D 1 . .
H H1A 0.240(7) 0.7000(9) 1.111(7) 0.045 Uiso d D 1 . .
H H2A 0.210(7) 0.6659(12) 1.307(5) 0.045 Uiso d D 1 . .
H H3A 0.034(5) 0.6623(12) 1.038(6) 0.045 Uiso d D 1 . .
C C1A 0.4093(5) 0.63963(10) 1.0854(5) 0.0275(6) Uani d . 1 . .
H H11A 0.5913 0.6446 1.2189 0.033 Uiso calc R 1 . .
C C2A 0.3164(7) 0.59156(11) 1.1079(7) 0.0416(8) Uani d . 1 . .
H H21A 0.3074 0.5877 1.2825 0.050 Uiso calc R 1 . .
H H22A 0.1314 0.5878 0.9823 0.050 Uiso calc R 1 . .
C C3A 0.4919(7) 0.55507(11) 1.0625(6) 0.0425(8) Uani d D 1 . .
C C4A 0.7301(9) 0.54142(17) 1.2477(11) 0.0857(16) Uani d D 1 . .
H H41A 0.7924 0.5561 1.4096 0.103 Uiso calc R 1 . .
C C5A 0.8839(10) 0.50614(19) 1.2023(12) 0.107(2) Uani d D 1 . .
H H51A 1.0491 0.4982 1.3320 0.128 Uiso calc R 1 . .
C C6A 0.7980(10) 0.48372(15) 0.9764(10) 0.0826(15) Uani d D 1 . .
H H61A 0.8957 0.4590 0.9504 0.099 Uiso calc R 1 . .
C C7A 0.5713(14) 0.4972(2) 0.7897(12) 0.122(2) Uani d D 1 . .
H H71A 0.5134 0.4826 0.6274 0.147 Uiso calc R 1 . .
C C8A 0.4192(12) 0.53240(18) 0.8317(9) 0.1005(19) Uani d D 1 . .
H H81A 0.2601 0.5410 0.6958 0.121 Uiso calc R 1 . .
C C9A 0.4199(5) 0.65037(10) 0.8121(5) 0.0254(6) Uani d . 1 . .
O O1B 0.8063(4) 0.74386(8) 1.1112(4) 0.0380(6) Uani d . 1 . .
O O2B 0.3534(4) 0.75444(7) 0.9634(4) 0.0351(5) Uani d . 1 . .
N N1B 0.8026(5) 0.73490(10) 0.6116(5) 0.0288(6) Uani d D 1 . .
H H1B 0.767(7) 0.7060(9) 0.641(7) 0.043 Uiso d D 1 . .
H H2B 0.979(5) 0.7419(12) 0.712(6) 0.043 Uiso d D 1 . .
H H3B 0.808(7) 0.7377(12) 0.441(5) 0.043 Uiso d D 1 . .
C C1B 0.5946(6) 0.76440(10) 0.6625(5) 0.0264(6) Uani d . 1 . .
H H11B 0.4140 0.7592 0.5273 0.032 Uiso calc R 1 . .
C C2B 0.6793(7) 0.81324(11) 0.6502(7) 0.0382(8) Uani d . 1 . .
H H21B 0.7254 0.8172 0.4926 0.046 Uiso calc R 1 . .
H H22B 0.8447 0.8190 0.8004 0.046 Uiso calc R 1 . .
C C3B 0.4638(8) 0.84833(12) 0.6484(8) 0.0508(9) Uani d . 1 . .
H H31B 0.3792 0.8392 0.7765 0.061 Uiso calc R 1 . .
C C4B 0.2403(9) 0.85166(17) 0.3812(9) 0.0764(13) Uani d . 1 . .
H H41B 0.1094 0.8742 0.3861 0.115 Uiso calc R 1 . .
H H42B 0.1493 0.8231 0.3356 0.115 Uiso calc R 1 . .
H H43B 0.3202 0.8598 0.2519 0.115 Uiso calc R 1 . .
C C5B 0.6026(13) 0.89361(16) 0.7332(12) 0.0970(18) Uani d . 1 . .
H H51B 0.4668 0.9157 0.7310 0.145 Uiso calc R 1 . .
H H52B 0.6938 0.9025 0.6142 0.145 Uiso calc R 1 . .
H H53B 0.7351 0.8912 0.9082 0.145 Uiso calc R 1 . .
C C6B 0.5822(5) 0.75299(9) 0.9353(5) 0.0250(6) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1A N1A H1A . . 111(2) ?
C1A N1A H2A . . 110(2) ?
H1A N1A H2A . . 111(3) ?
C1A N1A H3A . . 110(2) ?
H1A N1A H3A . . 111(3) ?
H2A N1A H3A . . 104(3) ?
N1A C1A C2A . . 106.7(2) ?
N1A C1A C9A . . 109.0(2) ?
C2A C1A C9A . . 113.0(2) ?
N1A C1A H11A . . 109.4 ?
C2A C1A H11A . . 109.4 ?
C9A C1A H11A . . 109.4 ?
C3A C2A C1A . . 116.1(2) ?
C3A C2A H21A . . 108.3 ?
C1A C2A H21A . . 108.3 ?
C3A C2A H22A . . 108.3 ?
C1A C2A H22A . . 108.3 ?
H21A C2A H22A . . 107.4 ?
C8A C3A C4A . . 115.1(4) ?
C8A C3A C2A . . 121.7(3) ?
C4A C3A C2A . . 123.2(3) ?
C3A C4A C5A . . 121.8(4) ?
C3A C4A H41A . . 119.1 ?
C5A C4A H41A . . 119.1 ?
C6A C5A C4A . . 120.8(4) ?
C6A C5A H51A . . 119.6 ?
C4A C5A H51A . . 119.6 ?
C7A C6A C5A . . 118.6(5) ?
C7A C6A H61A . . 120.7 ?
C5A C6A H61A . . 120.7 ?
C6A C7A C8A . . 120.9(5) ?
C6A C7A H71A . . 119.6 ?
C8A C7A H71A . . 119.6 ?
C3A C8A C7A . . 122.7(5) ?
C3A C8A H81A . . 118.7 ?
C7A C8A H81A . . 118.7 ?
O2A C9A O1A . . 126.0(2) ?
O2A C9A C1A . . 118.0(2) ?
O1A C9A C1A . . 116.0(2) ?
C1B N1B H1B . . 109(2) ?
C1B N1B H2B . . 113(2) ?
H1B N1B H2B . . 110(3) ?
C1B N1B H3B . . 114(2) ?
H1B N1B H3B . . 110(3) ?
H2B N1B H3B . . 102(3) ?
N1B C1B C2B . . 108.3(2) ?
N1B C1B C6B . . 108.9(2) ?
C2B C1B C6B . . 111.1(2) ?
N1B C1B H11B . . 109.5 ?
C2B C1B H11B . . 109.5 ?
C6B C1B H11B . . 109.5 ?
C1B C2B C3B . . 115.4(3) ?
C1B C2B H21B . . 108.4 ?
C3B C2B H21B . . 108.4 ?
C1B C2B H22B . . 108.4 ?
C3B C2B H22B . . 108.4 ?
H21B C2B H22B . . 107.5 ?
C4B C3B C5B . . 110.9(4) ?
C4B C3B C2B . . 111.5(3) ?
C5B C3B C2B . . 109.5(4) ?
C4B C3B H31B . . 108.3 ?
C5B C3B H31B . . 108.3 ?
C2B C3B H31B . . 108.3 ?
C3B C4B H41B . . 109.5 ?
C3B C4B H42B . . 109.5 ?
H41B C4B H42B . . 109.5 ?
C3B C4B H43B . . 109.5 ?
H41B C4B H43B . . 109.5 ?
H42B C4B H43B . . 109.5 ?
C3B C5B H51B . . 109.5 ?
C3B C5B H52B . . 109.5 ?
H51B C5B H52B . . 109.5 ?
C3B C5B H53B . . 109.5 ?
H51B C5B H53B . . 109.5 ?
H52B C5B H53B . . 109.5 ?
O2B C6B O1B . . 125.9(2) ?
O2B C6B C1B . . 118.0(2) ?
O1B C6B C1B . . 116.2(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C9A . 1.252(3) ?
O2A C9A . 1.240(3) ?
N1A C1A . 1.495(4) ?
N1A H1A . 0.93(3) ?
N1A H2A . 0.91(2) ?
N1A H3A . 0.90(2) ?
C1A C2A . 1.525(4) ?
C1A C9A . 1.534(3) ?
C1A H11A . 0.9800 ?
C2A C3A . 1.490(4) ?
C2A H21A . 0.9700 ?
C2A H22A . 0.9700 ?
C3A C8A . 1.353(5) ?
C3A C4A . 1.354(5) ?
C4A C5A . 1.389(6) ?
C4A H41A . 0.9300 ?
C5A C6A . 1.326(6) ?
C5A H51A . 0.9300 ?
C6A C7A . 1.318(6) ?
C6A H61A . 0.9300 ?
C7A C8A . 1.376(6) ?
C7A H71A . 0.9300 ?
C8A H81A . 0.9300 ?
O1B C6B . 1.250(3) ?
O2B C6B . 1.248(3) ?
N1B C1B . 1.488(4) ?
N1B H1B . 0.90(3) ?
N1B H2B . 0.91(2) ?
N1B H3B . 0.94(2) ?
C1B C2B . 1.524(4) ?
C1B C6B . 1.539(4) ?
C1B H11B . 0.9800 ?
C2B C3B . 1.526(5) ?
C2B H21B . 0.9700 ?
C2B H22B . 0.9700 ?
C3B C4B . 1.510(6) ?
C3B C5B . 1.519(6) ?
C3B H31B . 0.9800 ?
C4B H41B . 0.9600 ?
C4B H42B . 0.9600 ?
C4B H43B . 0.9600 ?
C5B H51B . 0.9600 ?
C5B H52B . 0.9600 ?
C5B H53B . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1A H1A O2B . 0.93(3) 1.98(3) 2.875(4) 161(3)
N1A H2A O1A 1_556 0.91(2) 1.82(3) 2.735(3) 176(3)
N1A H3A O2A 1_455 0.90(2) 2.03(3) 2.921(3) 174(3)
N1B H1B O2A . 0.90(3) 2.02(3) 2.896(4) 163(3)
N1B H2B O2B 1_655 0.91(2) 1.98(3) 2.887(3) 174(3)
N1B H3B O1B 1_554 0.94(2) 1.79(2) 2.729(3) 178(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1A C1A C2A C3A . . . . -179.9(3) ?
C9A C1A C2A C3A . . . . 60.4(3) ?
C1A C2A C3A C8A . . . . -101.7(5) ?
C1A C2A C3A C4A . . . . 79.8(5) ?
C8A C3A C4A C5A . . . . -1.0(8) ?
C2A C3A C4A C5A . . . . 177.6(5) ?
C3A C4A C5A C6A . . . . -1.7(10) ?
C4A C5A C6A C7A . . . . 3.8(10) ?
C5A C6A C7A C8A . . . . -3.0(11) ?
C4A C3A C8A C7A . . . . 1.8(9) ?
C2A C3A C8A C7A . . . . -176.8(6) ?
C6A C7A C8A C3A . . . . 0.2(11) ?
N1A C1A C9A O2A . . . . 140.2(3) ?
C2A C1A C9A O2A . . . . -101.4(3) ?
N1A C1A C9A O1A . . . . -40.2(3) ?
C2A C1A C9A O1A . . . . 78.2(3) ?
N1B C1B C2B C3B . . . . 169.4(3) ?
C6B C1B C2B C3B . . . . -71.1(3) ?
C1B C2B C3B C4B . . . . -76.9(4) ?
C1B C2B C3B C5B . . . . 159.9(4) ?
N1B C1B C6B O2B . . . . -143.5(3) ?
C2B C1B C6B O2B . . . . 97.3(3) ?
N1B C1B C6B O1B . . . . 37.8(3) ?
C2B C1B C6B O1B . . . . -81.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654162
