#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/43/2014327.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_2014327
loop_
_publ_author_name
'Görbitz, Carl Henrik'
'Bruvoll, Marius'
'Dizdarevic, Selma'
'Fimland, Nina'
'Hafizovic, Jasmina'
'Kalfjøs, Helen Therese'
'Krivokapic, Alexander'
'Vestli, Kristian'
_publ_section_title
;
 <small>L</small>-Isoleucyl-<small>L</small>-serine 0.33-hydrate,
 <small>L</small>-phenylalanyl-<small>L</small>-serine and
 <small>L</small>-methionyl-<small>L</small>-serine 0.34-hydrate
;
_journal_coeditor_code           FG1882
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o22
_journal_page_last               o25
_journal_paper_doi               10.1107/S0108270105038928
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H18 N2 O4 , 0.33H2 O'
_chemical_formula_moiety         'C9 H18 N2 O4 , 0.33H2 O'
_chemical_formula_sum            'C9 H18.67 N2 O4.33'
_chemical_formula_weight         224.27
_chemical_name_systematic
;
L-isoleucyl-L-serin 0.33-hydrate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.9420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9692(11)
_cell_length_b                   5.2167(3)
_cell_length_c                   12.4065(8)
_cell_measurement_reflns_used    3409
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      28.246
_cell_measurement_theta_min      2.401
_cell_volume                     1098.11(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method
'Sets of exposures each taken over 0.3° 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4482
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.8576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             485.4
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1454
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0524P)²+0.4828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                1373
_reflns_number_total             1454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1882.cif
_cod_data_source_block           IS
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2014327
_cod_database_fobs_code          2014327
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_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
_atom_site_type_symbol
O1 0.17779(8) 0.4492(3) 0.69462(12) 0.0240(3) Uani d . 1 . . O
O2 0.38873(8) 0.3939(3) 0.53174(11) 0.0245(3) Uani d . 1 . . O
H5 0.3846(16) 0.282(7) 0.582(2) 0.037 Uiso d . 1 . . H
O3 0.38543(8) 1.0734(3) 0.70512(12) 0.0232(3) Uani d . 1 . . O
O4 0.46639(7) 0.7373(3) 0.70364(12) 0.0269(3) Uani d . 1 . . O
N1 0.04799(8) 0.7822(4) 0.67305(12) 0.0189(3) Uani d . 1 . . N
H1 0.0597(14) 0.785(6) 0.601(2) 0.028 Uiso d . 1 . . H
H2 0.0076(15) 0.897(6) 0.684(2) 0.028 Uiso d . 1 . . H
H3 0.0287(15) 0.631(6) 0.692(2) 0.028 Uiso d . 1 . . H
N2 0.25631(8) 0.8009(3) 0.69495(12) 0.0160(3) Uani d . 1 . . N
H4 0.2567(13) 0.954(7) 0.7021(18) 0.019 Uiso d . 1 . . H
C1 0.11885(9) 0.8560(4) 0.73958(13) 0.0156(3) Uani d . 1 . . C
H11 0.1331 1.0372 0.7222 0.019 Uiso calc R 1 . . H
C2 0.09915(10) 0.8396(4) 0.86059(14) 0.0210(4) Uani d . 1 . . C
H21 0.0537 0.9569 0.8734 0.025 Uiso calc R 1 . . H
C4 0.14529(18) 0.9799(9) 1.04789(19) 0.0612(11) Uani d . 1 . . C
H41 0.1887 1.0669 1.0860 0.092 Uiso calc R 1 . . H
H42 0.1347 0.8154 1.0829 0.092 Uiso calc R 1 . . H
H43 0.0979 1.0873 1.0499 0.092 Uiso calc R 1 . . H
C3 0.16802(12) 0.9332(8) 0.93015(17) 0.0443(7) Uani d . 1 . . C
H31 0.1885 1.0947 0.8994 0.053 Uiso calc R 1 . . H
H32 0.2108 0.8044 0.9283 0.053 Uiso calc R 1 . . H
C5 0.0745(3) 0.5726(7) 0.8944(2) 0.0649(10) Uani d . 1 . . C
H51 0.0643 0.5711 0.9719 0.097 Uiso calc R 1 . . H
H52 0.1167 0.4509 0.8785 0.097 Uiso calc R 1 . . H
H53 0.0265 0.5233 0.8546 0.097 Uiso calc R 1 . . H
C6 0.18702(10) 0.6814(4) 0.70727(13) 0.0161(4) Uani d . 1 . . C
C7 0.32891(9) 0.6616(4) 0.67230(14) 0.0152(3) Uani d . 1 . . C
H71 0.3323 0.5059 0.7192 0.018 Uiso calc R 1 . . H
C8 0.32924(10) 0.5795(4) 0.55242(14) 0.0187(4) Uani d . 1 . . C
H81 0.2771 0.5073 0.5324 0.022 Uiso calc R 1 . . H
H82 0.3381 0.7323 0.5069 0.022 Uiso calc R 1 . . H
C9 0.39909(10) 0.8379(4) 0.69732(14) 0.0179(4) Uani d . 1 . . C
O1W 0.5000 0.9217(7) 0.5000 0.0284(10) Uani d SP 0.668(9) . . O
H1W 0.493(3) 0.807(11) 0.551(4) 0.043 Uiso d P 0.668(9) . . H
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
C8 O2 H5 105.2(19)
C1 N1 H1 110.4(15)
C1 N1 H2 110.3(17)
H1 N1 H2 107(2)
C1 N1 H3 112.2(16)
H1 N1 H3 111(2)
H2 N1 H3 105(2)
C6 N2 C7 122.26(16)
C6 N2 H4 117.1(16)
C7 N2 H4 120.7(16)
N1 C1 C6 107.81(14)
N1 C1 C2 109.67(13)
C6 C1 C2 113.43(14)
N1 C1 H11 108.6
C6 C1 H11 108.6
C2 C1 H11 108.6
C5 C2 C3 110.5(2)
C5 C2 C1 112.64(17)
C3 C2 C1 110.90(15)
C5 C2 H21 107.5
C3 C2 H21 107.5
C1 C2 H21 107.5
C3 C4 H41 109.5
C3 C4 H42 109.5
H41 C4 H42 109.5
C3 C4 H43 109.5
H41 C4 H43 109.5
H42 C4 H43 109.5
C2 C3 C4 112.81(18)
C2 C3 H31 109.0
C4 C3 H31 109.0
C2 C3 H32 109.0
C4 C3 H32 109.0
H31 C3 H32 107.8
C2 C5 H51 109.5
C2 C5 H52 109.5
H51 C5 H52 109.5
C2 C5 H53 109.5
H51 C5 H53 109.5
H52 C5 H53 109.5
O1 C6 N2 123.54(18)
O1 C6 C1 121.58(16)
N2 C6 C1 114.87(16)
N2 C7 C9 108.49(15)
N2 C7 C8 109.79(13)
C9 C7 C8 110.21(14)
N2 C7 H71 109.4
C9 C7 H71 109.4
C8 C7 H71 109.4
O2 C8 C7 112.00(14)
O2 C8 H81 109.2
C7 C8 H81 109.2
O2 C8 H82 109.2
C7 C8 H82 109.2
H81 C8 H82 107.9
O3 C9 O4 124.93(18)
O3 C9 C7 117.36(16)
O4 C9 C7 117.63(17)
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
O1 C6 . 1.231(2) ?
O2 C8 . 1.425(2) ?
O2 H5 . 0.86(3) ?
O3 C9 . 1.254(3) ?
O4 C9 . 1.258(2) ?
N1 C1 . 1.498(2) ?
N1 H1 . 0.92(3) ?
N1 H2 . 0.92(3) ?
N1 H3 . 0.89(3) ?
N2 C6 . 1.342(2) ?
N2 C7 . 1.462(2) ?
N2 H4 . 0.81(4) ?
C1 C6 . 1.531(2) ?
C1 C2 . 1.546(2) ?
C1 H11 . 1.0000 ?
C2 C5 . 1.515(4) ?
C2 C3 . 1.522(3) ?
C2 H21 . 1.0000 ?
C4 C3 . 1.536(3) ?
C4 H41 . 0.9800 ?
C4 H42 . 0.9800 ?
C4 H43 . 0.9800 ?
C3 H31 . 0.9900 ?
C3 H32 . 0.9900 ?
C5 H51 . 0.9800 ?
C5 H52 . 0.9800 ?
C5 H53 . 0.9800 ?
C7 C9 . 1.532(2) ?
C7 C8 . 1.548(2) ?
C7 H71 . 1.0000 ?
C8 H81 . 0.9900 ?
C8 H82 . 0.9900 ?
O1W H1W . 0.88(5) ?
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
_geom_hbond_publ_flag
N1 H1 O2 4_556 0.92(3) 1.95(2) 2.8353(17) 158(2) y
N1 H2 O4 3_455 0.92(3) 1.95(3) 2.777(2) 153(2) y
N1 H3 O4 3_445 0.89(3) 2.31(3) 3.187(2) 167.0(18) y
N1 H3 O3 3_445 0.89(3) 2.46(2) 2.9983(17) 119.7(17) y
N2 H4 O3 1_555 0.81(4) 2.26(2) 2.6132(18) 106.0(16) y
O2 H5 O3 1_545 0.86(3) 1.88(3) 2.7258(18) 172(2) y
C1 H11 O1 1_565 1.00 2.31 3.302(2) 174 y
C7 H71 O3 1_545 1.00 2.44 3.240(2) 137 y
O1W H1W O4 1_555 0.88(5) 1.99(4) 2.771(17) 149(4) y
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_publ_flag
N1 C1 C6 N2 136.37(16) y
C1 C6 N2 C7 175.27(14) y
C6 N2 C7 C9 -162.77(16) y
N2 C7 C9 O3 -17.1(2) y
N1 C1 C2 C3 -175.7(2) y
N1 C1 C2 C5 59.9(3) y
C1 C2 C3 C4 166.7(3) y
N2 C7 C8 O2 -166.25(15) y
C7 C8 O2 H5 45.9(17) y
C6 C1 C2 C5 -60.7(3) ?
C6 C1 C2 C3 63.8(2) ?
C5 C2 C3 C4 -67.7(4) ?
C7 N2 C6 O1 -4.3(3) ?
N1 C1 C6 O1 -44.1(2) ?
C2 C1 C6 O1 77.6(2) ?
C2 C1 C6 N2 -102.00(18) ?
C6 N2 C7 C8 76.7(2) ?
C9 C7 C8 O2 74.30(19) ?
C8 C7 C9 O3 103.17(19) ?
N2 C7 C9 O4 166.06(15) ?
C8 C7 C9 O4 -73.7(2) ?
