#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/01/2310143.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_2310143
loop_
_publ_author_name
'Woińska, Magdalena'
'Jayatilaka, Dylan'
'Spackman, Mark A.'
'Edwards, Alison J.'
'Dominiak, Paulina M.'
'Woźniak, Krzysztof'
'Nishibori, Eiji'
'Sugimoto, Kunihisa'
'Grabowsky, Simon'
_publ_section_title
;
 Hirshfeld atom refinement for modelling strong hydrogen bonds
;
_journal_coeditor_code           KX5029
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section A'
_journal_page_first              483
_journal_page_last               498
_journal_paper_doi               10.1107/S2053273314012443
_journal_volume                  70
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H12 N O2, C4 H3 O4'
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.27
_chemical_name_common            'L-phenylalaninium hydrogen maleate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.36(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.905(2)
_cell_length_b                   5.2338(10)
_cell_length_c                   11.439(2)
_cell_measurement_reflns_used    124185
_cell_measurement_temperature    25
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      0.90
_cell_volume                     640.1(2)
_diffrn_ambient_temperature      25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SPring-8 BL02B1 Imaging plate camera'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.3540
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            124185
_diffrn_reflns_theta_full        23.16
_diffrn_reflns_theta_max         23.16
_diffrn_reflns_theta_min         0.90
_exptl_absorpt_coefficient_mu    0.039
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.86
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    211
_refine_ls_number_parameters     105
_refine_ls_number_reflns         7370
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0201
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_wR_factor_gt          0.0211
_reflns_number_gt                7370
_reflns_number_total             7820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            kx5029sup1.cif
_cod_data_source_block           xray
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C13 H15 N1 O6'
_cod_database_code               2310143
_cod_database_fobs_code          2310143
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_occupancy
O1 0.09516(2) 0.4786(3) -0.38078(2) Uani 1
O2 0.12318(2) 0.5095(3) -0.58415(2) Uani 1
O3 0.13521(2) 0.7084(3) -0.21652(2) Uani 1
O4 0.17832(2) 0.8004(3) -0.70331(2) Uani 1
C1 0.13464(2) 0.6824(3) -0.32530(2) Uani 1
C2 0.18015(2) 0.9012(3) -0.38884(2) Uani 1
C3 0.18958(2) 0.9238(3) -0.50385(2) Uani 1
C4 0.16122(2) 0.7356(3) -0.60348(2) Uani 1
H1 0.108(1) 0.490(3) -0.482(1) Uani 1
H2 0.205(1) 1.067(2) -0.3353(8) Uani 1
H3 0.223(1) 1.103(2) -0.5310(8) Uani 1
O5 0.22350(2) 1.0886(3) -0.09277(2) Uani 1
O6 0.09514(2) 0.9225(3) 0.01777(2) Uani 1
N1 0.12387(2) 1.2983(3) 0.17420(2) Uani 1
C5 0.16349(2) 1.0922(3) -0.00443(2) Uani 1
C6 0.18067(2) 1.3373(3) 0.06745(2) Uani 1
C7 0.31499(2) 1.4370(3) 0.10137(2) Uani 1
C8 0.40364(2) 1.2627(3) 0.18246(2) Uani 1
C9 0.41968(2) 1.2878(3) 0.30620(2) Uani 1
C10 0.49986(3) 1.1253(3) 0.38180(2) Uani 1
C11 0.56582(2) 0.9369(3) 0.33443(2) Uani 1
C12 0.55181(2) 0.9116(3) 0.21135(2) Uani 1
C13 0.47072(2) 1.0735(3) 0.13591(2) Uani 1
H41 0.137(1) 1.462(2) 0.2237(9) Uani 1
H42 0.1611(9) 1.145(2) 0.2191(9) Uani 1
H43 0.0284(8) 1.259(2) 0.1514(9) Uani 1
H5 0.191(1) 0.936(3) -0.147(1) Uani 1
H6 0.1241(8) 1.484(2) 0.0128(8) Uani 1
H71 0.3113(9) 1.624(2) 0.1428(8) Uani 1
H72 0.3460(9) 1.469(2) 0.0183(7) Uani 1
H9 0.3685(8) 1.440(2) 0.3399(8) Uani 1
H10 0.5120(9) 1.146(2) 0.4803(7) Uani 1
H11 0.6284(9) 0.811(2) 0.3954(8) Uani 1
H12 0.6043(9) 0.768(2) 0.1718(8) Uani 1
H13 0.4605(9) 1.056(2) 0.0400(8) Uani 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O3 121.50(12)
O2 C4 O4 121.44(11)
O5 C5 O6 124.79(13)
O1 C1 C2 120.84(6)
O2 C4 C3 120.07(6)
O3 C1 C2 117.65(13)
O4 C4 C3 118.47(13)
O5 C5 C6 113.85(11)
O6 C5 C6 121.30(6)
O1 H1 O2 178.(1)
C1 O1 H1 110.4(7)
C4 O2 H1 110.5(7)
C5 O5 H5 108.1(6)
C1 C2 C3 129.84(12)
C2 C3 C4 130.16(13)
C5 C6 C7 115.84(7)
C6 C7 C8 114.53(11)
C7 C8 C9 120.21(10)
C7 C8 C13 120.97(5)
C8 C9 C10 120.64(10)
C8 C13 C12 120.70(5)
C9 C8 C13 118.82(9)
C9 C10 C11 120.04(5)
C10 C11 C12 119.93(9)
C11 C12 C13 119.87(10)
C1 C2 H2 114.5(5)
C2 C3 H3 117.1(5)
C3 C2 H2 115.6(5)
C4 C3 H3 112.7(5)
C5 C6 H6 106.7(5)
C6 C7 H71 107.5(5)
C6 C7 H72 106.2(5)
C7 C6 H6 107.9(5)
C8 C7 H71 110.4(5)
C8 C7 H72 111.1(5)
C8 C9 H9 117.3(5)
C8 C13 H13 119.1(5)
C9 C10 H10 120.4(6)
C10 C9 H9 122.1(5)
C10 C11 H11 119.0(5)
C11 C10 H10 119.6(6)
C11 C12 H12 121.4(5)
C12 C11 H11 121.1(5)
C12 C13 H13 120.2(5)
C13 C12 H12 118.7(5)
C6 N1 H41 107.8(6)
C6 N1 H42 109.9(5)
C6 N1 H43 112.3(5)
H71 C7 H72 106.7(8)
H41 N1 H42 113.2(8)
H41 N1 H43 109.1(9)
H42 N1 H43 104.7(9)
N1 C6 C5 107.59(11)
N1 C6 C7 111.77(2)
N1 C6 H6 106.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2721(19)
O1 H1 1.192(8)
O2 C4 1.287(2)
O2 H1 1.219(8)
O3 C1 1.2506(5)
O4 C4 1.2401(7)
C1 C2 1.4927(17)
C2 C3 1.3449(5)
C2 H2 1.065(5)
C3 C4 1.4919(15)
C3 H3 1.074(11)
O5 C5 1.3078(2)
O5 H5 1.026(7)
O6 C5 1.2180(17)
N1 H41 1.022(10)
N1 H42 0.996(10)
N1 H43 1.044(9)
C5 C6 1.5153(19)
C6 C7 1.5312(9)
C6 H6 1.100(5)
C7 C8 1.5080(14)
C7 H71 1.089(5)
C7 H72 1.082(4)
C8 C9 1.3978(5)
C8 C13 1.3974(16)
C9 C10 1.3921(14)
C9 H9 1.085(5)
C10 C11 1.3917(16)
C10 H10 1.114(4)
C11 C12 1.3923(5)
C11 H11 1.096(5)
C12 C13 1.3943(14)
C12 H12 1.095(5)
C13 H13 1.085(9)
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
O3 C1 O1 H1 -176.8(7)
O4 C4 O2 H1 -177.5(7)
O6 C5 O5 H5 9.5(8)
O1 C1 C2 C3 -1.09(4)
O2 C4 C3 C2 -1.36(4)
O3 C1 C2 C3 179.88(8)
O4 C4 C3 C2 -179.50(3)
O5 C5 C6 C7 -45.70(3)
O6 C5 C6 C7 137.11(2)
O1 C1 C2 H2 175.7(7)
O2 C4 C3 H3 178.1(7)
O3 C1 C2 H2 -3.3(7)
O4 C4 C3 H3 -0.0(7)
O5 C5 C6 H6 74.4(5)
O6 C5 C6 H6 -102.8(5)
O5 C5 C6 N1 -171.56(2)
O6 C5 C6 N1 11.24(3)
C2 C1 O1 H1 4.1(7)
C3 C4 O2 H1 4.5(7)
C6 C5 O5 H5 -167.6(8)
C1 C2 C3 C4 -1.99(5)
C5 C6 C7 C8 -63.64(3)
C6 C7 C8 C9 -90.20(3)
C6 C7 C8 C13 89.62(3)
C7 C8 C9 C10 179.03(3)
C7 C8 C13 C12 -179.49(10)
C8 C9 C10 C11 0.53(4)
C8 C13 C12 C11 0.41(4)
C9 C8 C13 C12 0.32(4)
C9 C10 C11 C12 0.19(16)
C10 C9 C8 C13 -0.79(4)
C10 C11 C12 C13 -0.68(4)
C1 C2 C3 H3 178.6(7)
C4 C3 C2 H2 -178.8(7)
C5 C6 C7 H71 173.3(6)
C5 C6 C7 H72 59.4(6)
C7 C8 C9 H9 -1.9(6)
C7 C8 C13 H13 1.8(6)
C8 C7 C6 H6 176.9(5)
C8 C9 C10 H10 -180.0(6)
C8 C13 C12 H12 -178.7(7)
C9 C8 C7 H71 31.2(6)
C9 C8 C7 H72 149.4(6)
C9 C8 C13 H13 -178.4(6)
C9 C10 C11 H11 -180.0(6)
C10 C11 C12 H12 178.5(7)
C11 C10 C9 H9 -178.5(6)
C11 C12 C13 H13 179.1(6)
C12 C11 C10 H10 -179.5(6)
C13 C8 C7 H71 -148.9(6)
C13 C8 C7 H72 -30.7(6)
C13 C8 C9 H9 178.3(6)
C13 C12 C11 H11 179.5(7)
C5 C6 N1 H41 179.0(6)
C5 C6 N1 H42 55.2(7)
C5 C6 N1 H43 -60.9(7)
C7 C6 N1 H41 50.7(6)
C7 C6 N1 H42 -73.0(7)
C7 C6 N1 H43 170.9(7)
H2 C2 C3 H3 2.(1)
H6 C6 C7 H71 53.8(8)
H6 C6 C7 H72 -60.1(8)
H9 C9 C10 H10 1.2(9)
H10 C10 C11 H11 0.4(9)
H11 C11 C12 H12 -1.(1)
H12 C12 C13 H13 -0.0(9)
H41 N1 C6 H6 -66.8(9)
H42 N1 C6 H6 169.4(9)
H43 N1 C6 H6 53.3(9)
N1 C6 C7 C8 60.06(14)
N1 C6 C7 H71 -63.0(6)
N1 C6 C7 H72 -176.9(6)
