#------------------------------------------------------------------------------
#$Date: 2025-01-25 05:16:05 +0200 (Sat, 25 Jan 2025) $
#$Revision: 297468 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312742.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_2312742
loop_
_publ_author_name
'Movilla, Federico'
'Rey, Juan Manuel'
'López Borda, María Del Rosario'
'Di Salvo, Florencia'
_publ_section_title
;
 Conformational versatility among crystalline solids of L-phenylalanine
 derivatives.
;
_journal_coeditor_code           ZO3057
_journal_issue                   2
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229625000269
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C20 H19 N O2'
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_chemical_name_systematic
;
2-[(Naphthalen-2-ylmethyl)azaniumyl]-3-phenylpropanoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                91.113(9)
_cell_angle_beta                 91.423(9)
_cell_angle_gamma                96.92(2)
_cell_formula_units_Z            2
_cell_length_a                   5.620(3)
_cell_length_b                   8.620(3)
_cell_length_c                   16.070(5)
_cell_measurement_reflns_used    6357
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.794
_cell_measurement_theta_min      1.196
_cell_volume                     772.4(5)
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device_type  'custom air-bearing with MK3 mini-kappa'
_diffrn_measurement_method       'shuterless φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.67019
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35270
_diffrn_reflns_theta_full        23.710
_diffrn_reflns_theta_max         28.794
_diffrn_reflns_theta_min         1.196
_diffrn_source                   Sirius-MANACA
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9656716
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(XDS; Kabsch, 2010)
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       irregular
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0417
_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)+(0.0705P)²+0.1829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                3429
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zo3057sup1.cif
_cod_data_source_block           pn_p-1
_cod_database_code               2312742
_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   0.978
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.27570(13) 0.09582(9) 0.52374(5) 0.02534(18) Uani d 1 . .
O O2 0.21306(13) 0.34651(9) 0.52230(5) 0.02386(18) Uani d 1 . .
N N1 0.75195(15) 0.23188(10) 0.47684(5) 0.01926(18) Uani d 1 . .
H H1A 0.911753 0.257036 0.487758 0.023 Uiso calc 1 . .
H H1B 0.721933 0.125861 0.472673 0.023 Uiso calc 1 . .
C C8 0.34427(17) 0.23905(12) 0.53057(6) 0.0194(2) Uani d 1 . .
C C11 0.82750(18) 0.24354(12) 0.32342(6) 0.0209(2) Uani d 1 . .
C C20 1.02529(18) 0.15809(12) 0.33487(6) 0.0219(2) Uani d 1 . .
H H20 1.070189 0.129172 0.389262 0.026 Uiso calc 1 . .
C C18 1.08958(19) 0.15691(12) 0.18562(7) 0.0223(2) Uani d 1 . .
C C9 0.61511(17) 0.28866(11) 0.54835(6) 0.0193(2) Uani d 1 . .
H H9 0.647475 0.405056 0.554112 0.023 Uiso calc 1 . .
C C4 0.60382(18) 0.26650(12) 0.70681(6) 0.0224(2) Uani d 1 . .
C C13 0.88862(18) 0.24002(12) 0.17343(6) 0.0226(2) Uani d 1 . .
C C19 1.15292(18) 0.11666(12) 0.26760(7) 0.0227(2) Uani d 1 . .
H H19 1.285957 0.060017 0.276327 0.027 Uiso calc 1 . .
C C12 0.76030(18) 0.28210(12) 0.24395(7) 0.0224(2) Uani d 1 . .
H H12 0.625790 0.337793 0.236219 0.027 Uiso calc 1 . .
C C10 0.68883(18) 0.29949(12) 0.39557(6) 0.0215(2) Uani d 1 . .
H H10A 0.720300 0.414859 0.400297 0.026 Uiso calc 1 . .
H H10B 0.515166 0.271491 0.383566 0.026 Uiso calc 1 . .
C C3 0.38532(19) 0.19369(13) 0.73486(7) 0.0257(2) Uani d 1 . .
H H3 0.295966 0.113644 0.701616 0.031 Uiso calc 1 . .
C C7 0.70616(18) 0.21310(13) 0.62652(6) 0.0234(2) Uani d 1 . .
H H7A 0.666808 0.098294 0.620494 0.028 Uiso calc 1 . .
H H7B 0.882999 0.236362 0.630322 0.028 Uiso calc 1 . .
C C14 0.8241(2) 0.27914(14) 0.09074(7) 0.0266(2) Uani d 1 . .
H H14 0.688583 0.333195 0.081313 0.032 Uiso calc 1 . .
C C17 1.2221(2) 0.11606(13) 0.11573(7) 0.0256(2) Uani d 1 . .
H H17 1.356146 0.059947 0.123612 0.031 Uiso calc 1 . .
C C16 1.1571(2) 0.15741(14) 0.03702(7) 0.0289(2) Uani d 1 . .
H H16 1.247542 0.130870 -0.009207 0.035 Uiso calc 1 . .
C C5 0.73045(19) 0.38546(13) 0.75628(7) 0.0263(2) Uani d 1 . .
H H5 0.877599 0.437351 0.737600 0.032 Uiso calc 1 . .
C C6 0.6433(2) 0.42886(13) 0.83272(7) 0.0290(2) Uani d 1 . .
H H6 0.731467 0.509444 0.865941 0.035 Uiso calc 1 . .
C C2 0.2975(2) 0.23736(14) 0.81099(7) 0.0290(2) Uani d 1 . .
H H2 0.148634 0.187340 0.829298 0.035 Uiso calc 1 . .
C C1 0.4272(2) 0.35405(14) 0.86031(7) 0.0296(2) Uani d 1 . .
H H1 0.368456 0.382593 0.912658 0.036 Uiso calc 1 . .
C C15 0.9566(2) 0.23916(14) 0.02451(7) 0.0296(2) Uani d 1 . .
H H15 0.912727 0.266871 -0.030198 0.035 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0026 0.0014 '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 0.0052 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0094 0.0054 '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
H1A N1 H1B . . 107.8 ?
C9 N1 H1A . . 108.9 ?
C9 N1 H1B . . 108.9 ?
C10 N1 H1A . . 108.9 ?
C10 N1 H1B . . 108.9 ?
C10 N1 C9 . . 113.16(8) ?
O1 C8 O2 . . 125.61(10) ?
O1 C8 C9 . . 117.20(9) ?
O2 C8 C9 . . 117.17(9) ?
C20 C11 C10 . . 122.57(9) ?
C12 C11 C20 . . 119.41(10) ?
C12 C11 C10 . . 117.99(9) ?
C11 C20 H20 . . 119.8 ?
C19 C20 C11 . . 120.36(10) ?
C19 C20 H20 . . 119.8 ?
C13 C18 C17 . . 119.61(10) ?
C19 C18 C13 . . 118.74(10) ?
C19 C18 C17 . . 121.65(10) ?
N1 C9 C8 . . 108.34(8) ?
N1 C9 H9 . . 109.9 ?
N1 C9 C7 . . 106.46(8) ?
C8 C9 H9 . . 109.9 ?
C7 C9 C8 . . 112.17(8) ?
C7 C9 H9 . . 109.9 ?
C3 C4 C7 . . 120.74(10) ?
C5 C4 C3 . . 118.61(10) ?
C5 C4 C7 . . 120.60(10) ?
C18 C13 C12 . . 118.96(10) ?
C18 C13 C14 . . 118.59(10) ?
C12 C13 C14 . . 122.45(10) ?
C20 C19 C18 . . 121.25(10) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C11 C12 C13 . . 121.27(10) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
N1 C10 C11 . . 113.37(9) ?
N1 C10 H10A . . 108.9 ?
N1 C10 H10B . . 108.9 ?
C11 C10 H10A . . 108.9 ?
C11 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C4 C3 H3 . . 119.7 ?
C2 C3 C4 . . 120.68(10) ?
C2 C3 H3 . . 119.7 ?
C9 C7 H7A . . 108.6 ?
C9 C7 H7B . . 108.6 ?
C4 C7 C9 . . 114.50(9) ?
C4 C7 H7A . . 108.6 ?
C4 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
C13 C14 H14 . . 119.8 ?
C15 C14 C13 . . 120.49(11) ?
C15 C14 H14 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C16 C17 C18 . . 120.32(11) ?
C16 C17 H17 . . 119.8 ?
C17 C16 H16 . . 119.9 ?
C17 C16 C15 . . 120.30(10) ?
C15 C16 H16 . . 119.9 ?
C4 C5 H5 . . 119.6 ?
C6 C5 C4 . . 120.78(10) ?
C6 C5 H5 . . 119.6 ?
C5 C6 H6 . . 120.0 ?
C1 C6 C5 . . 119.97(11) ?
C1 C6 H6 . . 120.0 ?
C3 C2 H2 . . 119.9 ?
C1 C2 C3 . . 120.15(10) ?
C1 C2 H2 . . 119.9 ?
C6 C1 H1 . . 120.1 ?
C2 C1 C6 . . 119.79(11) ?
C2 C1 H1 . . 120.1 ?
C14 C15 C16 . . 120.68(11) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
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 C8 . 1.2501(13) ?
O2 C8 . 1.2586(14) ?
N1 H1A . 0.9100 ?
N1 H1B . 0.9100 ?
N1 C9 . 1.5048(13) ?
N1 C10 . 1.4924(13) ?
C8 C9 . 1.5486(16) ?
C11 C20 . 1.4158(16) ?
C11 C12 . 1.3809(15) ?
C11 C10 . 1.5160(14) ?
C20 H20 . 0.9500 ?
C20 C19 . 1.3769(15) ?
C18 C13 . 1.4201(17) ?
C18 C19 . 1.4167(15) ?
C18 C17 . 1.4246(15) ?
C9 H9 . 1.0000 ?
C9 C7 . 1.5311(15) ?
C4 C3 . 1.3992(16) ?
C4 C7 . 1.5116(15) ?
C4 C5 . 1.3980(16) ?
C13 C12 . 1.4224(15) ?
C13 C14 . 1.4262(15) ?
C19 H19 . 0.9500 ?
C12 H12 . 0.9500 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C3 H3 . 0.9500 ?
C3 C2 . 1.3926(16) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C14 H14 . 0.9500 ?
C14 C15 . 1.3759(16) ?
C17 H17 . 0.9500 ?
C17 C16 . 1.3734(17) ?
C16 H16 . 0.9500 ?
C16 C15 . 1.4116(18) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.3945(16) ?
C6 H6 . 0.9500 ?
C6 C1 . 1.3917(17) ?
C2 H2 . 0.9500 ?
C2 C1 . 1.3911(17) ?
C1 H1 . 0.9500 ?
C15 H15 . 0.9500 ?
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
O1 C8 C9 N1 . . . . 61.47(11) ?
O1 C8 C9 C7 . . . . -55.75(12) ?
O2 C8 C9 N1 . . . . -116.92(9) ?
O2 C8 C9 C7 . . . . 125.86(10) ?
N1 C9 C7 C4 . . . . 175.23(8) ?
C8 C9 C7 C4 . . . . -66.43(12) ?
C11 C20 C19 C18 . . . . -0.48(16) ?
C20 C11 C12 C13 . . . . -1.13(15) ?
C20 C11 C10 N1 . . . . -10.39(13) ?
C18 C13 C12 C11 . . . . -0.06(15) ?
C18 C13 C14 C15 . . . . -1.04(16) ?
C18 C17 C16 C15 . . . . -0.76(17) ?
C9 N1 C10 C11 . . . . 179.59(7) ?
C4 C3 C2 C1 . . . . -0.22(18) ?
C4 C5 C6 C1 . . . . -0.38(18) ?
C13 C18 C19 C20 . . . . -0.71(15) ?
C13 C18 C17 C16 . . . . 0.35(16) ?
C13 C14 C15 C16 . . . . 0.66(18) ?
C19 C18 C13 C12 . . . . 0.98(15) ?
C19 C18 C13 C14 . . . . -179.45(9) ?
C19 C18 C17 C16 . . . . -179.66(10) ?
C12 C11 C20 C19 . . . . 1.41(15) ?
C12 C11 C10 N1 . . . . 171.45(9) ?
C12 C13 C14 C15 . . . . 178.52(10) ?
C10 N1 C9 C8 . . . . 60.96(10) ?
C10 N1 C9 C7 . . . . -178.22(8) ?
C10 C11 C20 C19 . . . . -176.72(9) ?
C10 C11 C12 C13 . . . . 177.09(9) ?
C3 C4 C7 C9 . . . . 86.18(13) ?
C3 C4 C5 C6 . . . . 1.17(16) ?
C3 C2 C1 C6 . . . . 1.03(18) ?
C7 C4 C3 C2 . . . . 176.54(10) ?
C7 C4 C5 C6 . . . . -176.25(10) ?
C14 C13 C12 C11 . . . . -179.61(10) ?
C17 C18 C13 C12 . . . . -179.03(9) ?
C17 C18 C13 C14 . . . . 0.54(15) ?
C17 C18 C19 C20 . . . . 179.30(9) ?
C17 C16 C15 C14 . . . . 0.25(18) ?
C5 C4 C3 C2 . . . . -0.87(17) ?
C5 C4 C7 C9 . . . . -96.46(12) ?
C5 C6 C1 C2 . . . . -0.73(18) ?

_cod_database_fobs_code 2312742
