#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:03:49 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244163.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_7244163
loop_
_publ_author_name
'Gong, Yaxiang'
'Wei, Yuanfeng'
'Gao, Yuan'
'Pang, Zunting'
'Zhang, Jianjun'
'Qian, Shuai'
_publ_section_title
;
 The bending behavior of an L-phenylalanine monohydrate soft crystal
 via reversible hydrogen bond rupture and remodeling.
;
_journal_issue                   5
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              3216
_journal_page_last               3221
_journal_paper_doi               10.1039/d1cp05449j
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.611(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0612(5)
_cell_length_b                   5.4197(2)
_cell_length_c                   13.8643(6)
_cell_measurement_reflns_used    9068
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.95
_cell_measurement_theta_min      2.84
_cell_volume                     957.75(7)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17880
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.011
_diffrn_reflns_theta_min         2.841
_exptl_absorpt_coefficient_mu    0.506
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0442P)²+0.0888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3131
_reflns_number_total             3504
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp05449j3.cif
_cod_data_source_block           20200601zh_ykd_chenhui_0m_a
_cod_depositor_comments          'Adding full bibliography for 7244163.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244163
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85578(19) 0.8362(4) 0.34864(18) 0.0403(6) Uani 1 1 d . . . . .
H1 H 0.850250 0.981663 0.309626 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7866(2) 0.7986(5) 0.41012(19) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.733364 0.916648 0.412174 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7951(2) 0.5892(5) 0.46856(18) 0.0445(6) Uani 1 1 d . . . . .
H3 H 0.748321 0.564194 0.511387 0.053 Uiso 1 1 calc R U . . .
C4 C 0.8718(2) 0.4173(5) 0.46423(19) 0.0451(6) Uani 1 1 d . . . . .
H4 H 0.877665 0.272990 0.503950 0.054 Uiso 1 1 calc R U . . .
C5 C 0.94024(19) 0.4547(5) 0.40203(18) 0.0407(6) Uani 1 1 d . . . . .
H5 H 0.992832 0.335166 0.399599 0.049 Uiso 1 1 calc R U . . .
C6 C 0.93316(18) 0.6638(4) 0.34330(17) 0.0369(5) Uani 1 1 d . . . . .
C7 C 1.00799(18) 0.7074(4) 0.27633(18) 0.0408(6) Uani 1 1 d . . . . .
H7A H 1.073335 0.614083 0.302356 0.049 Uiso 1 1 calc R U . . .
H7B H 1.026327 0.884888 0.278522 0.049 Uiso 1 1 calc R U . . .
C8 C 0.96567(17) 0.6327(4) 0.16798(18) 0.0336(5) Uani 1 1 d . . . . .
H8 H 1.019445 0.676147 0.129346 0.040 Uiso 1 1 calc R U . . .
C9 C 0.94605(18) 0.3549(4) 0.15950(18) 0.0349(5) Uani 1 1 d . . . . .
C10 C 0.3969(2) 0.2493(5) 0.28018(18) 0.0467(6) Uani 1 1 d . . . . .
H10 H 0.387770 0.106788 0.239310 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3158(2) 0.3292(6) 0.3220(2) 0.0571(8) Uani 1 1 d . . . . .
H11 H 0.251003 0.242611 0.308996 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3286(2) 0.5325(7) 0.3819(2) 0.0582(8) Uani 1 1 d . . . . .
H12 H 0.272679 0.586347 0.410556 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4217(2) 0.6588(6) 0.4007(2) 0.0553(7) Uani 1 1 d . . . . .
H13 H 0.430716 0.798792 0.442910 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5029(2) 0.5816(5) 0.35788(19) 0.0438(6) Uani 1 1 d . . . . .
H14 H 0.566999 0.671022 0.370161 0.053 Uiso 1 1 calc R U . . .
C15 C 0.49139(19) 0.3758(4) 0.29754(17) 0.0350(5) Uani 1 1 d . . . . .
C16 C 0.57871(18) 0.2901(4) 0.24921(16) 0.0363(5) Uani 1 1 d . . . . .
H16A H 0.586841 0.109097 0.256974 0.044 Uiso 1 1 calc R U . . .
H16B H 0.645462 0.367751 0.283225 0.044 Uiso 1 1 calc R U . . .
C17 C 0.55711(16) 0.3551(4) 0.13905(16) 0.0282(5) Uani 1 1 d . . . . .
H17 H 0.485485 0.295235 0.106469 0.034 Uiso 1 1 calc R U . . .
C18 C 0.56277(16) 0.6346(4) 0.12347(15) 0.0280(5) Uani 1 1 d . . . . .
N1 N 0.86681(13) 0.7649(3) 0.12414(14) 0.0318(4) Uani 1 1 d . . . . .
H1A H 0.849656 0.737030 0.057840 0.048 Uiso 1 1 calc R U . . .
H1B H 0.875883 0.929652 0.135602 0.048 Uiso 1 1 calc R U . . .
H1C H 0.814331 0.709087 0.152133 0.048 Uiso 1 1 calc R U . . .
N2 N 0.63602(13) 0.2302(3) 0.09311(13) 0.0313(4) Uani 1 1 d . . . . .
H2A H 0.618094 0.249973 0.026357 0.047 Uiso 1 1 calc R U . . .
H2B H 0.637867 0.066497 0.107972 0.047 Uiso 1 1 calc R U . . .
H2C H 0.700375 0.297726 0.116886 0.047 Uiso 1 1 calc R U . . .
O1 O 1.02439(15) 0.2207(3) 0.16521(17) 0.0621(6) Uani 1 1 d . . . . .
O2 O 0.85432(12) 0.2792(3) 0.15202(12) 0.0385(4) Uani 1 1 d . . . . .
O3 O 0.65238(11) 0.7246(3) 0.12868(13) 0.0409(4) Uani 1 1 d . . . . .
O4 O 0.47964(12) 0.7564(3) 0.10843(11) 0.0358(4) Uani 1 1 d . . . . .
O5 O 0.26837(14) 0.6826(4) 0.10208(16) 0.0707(7) Uani 1 1 d . . . . .
H5A H 0.244042 0.506757 0.107027 0.085 Uiso 1 1 d R U . . .
H5B H 0.336042 0.684057 0.126327 0.085 Uiso 1 1 d R U . . .
O6 O 0.18299(14) 0.1613(4) 0.07538(13) 0.0592(6) Uani 1 1 d . . . . .
H6A H 0.214689 -0.012247 0.084966 0.071 Uiso 1 1 d R U . . .
H6B H 0.140189 0.190253 0.111866 0.071 Uiso 1 1 d R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
_geom_angle_publ_flag
C2 C1 C6 120.9(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 121.4(2) . . ?
C1 C6 C7 120.3(2) . . ?
C6 C7 C8 114.68(18) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C9 109.13(18) . . ?
N1 C8 C7 111.56(18) . . ?
C9 C8 C7 110.7(2) . . ?
N1 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
O1 C9 O2 125.0(2) . . ?
O1 C9 C8 116.7(2) . . ?
O2 C9 C8 118.15(19) . . ?
C11 C10 C15 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C15 C10 H10 119.8 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 118.6(2) . . ?
C14 C15 C16 121.4(2) . . ?
C10 C15 C16 119.9(2) . . ?
C15 C16 C17 112.17(18) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 109.15(17) . . ?
N2 C17 C18 109.26(17) . . ?
C16 C17 C18 111.31(18) . . ?
N2 C17 H17 109.0 . . ?
C16 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
O4 C18 O3 124.8(2) . . ?
O4 C18 C17 118.58(18) . . ?
O3 C18 C17 116.65(19) . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C17 N2 H2A 109.5 . . ?
C17 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C17 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
H5A O5 H5B 106.8 . . ?
H6A O6 H6B 113.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(4) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.506(3) . ?
C7 C8 1.537(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.486(3) . ?
C8 C9 1.528(3) . ?
C8 H8 1.0000 . ?
C9 O1 1.244(3) . ?
C9 O2 1.249(3) . ?
C10 C11 1.383(4) . ?
C10 C15 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.516(3) . ?
C16 C17 1.532(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N2 1.488(3) . ?
C17 C18 1.534(3) . ?
C17 H17 1.0000 . ?
C18 O4 1.249(3) . ?
C18 O3 1.255(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
O5 H5A 1.0117 . ?
O5 H5B 0.8744 . ?
O6 H6A 1.0245 . ?
O6 H6B 0.8465 . ?
