Second harmonic generation and crystal structure of a self-assembled Boc-p-nitro-l-phenylalanyl-p-nitro-l-phenylalanine dipeptide
Baptista, Rosa M. F.; Ayala, Alejandro P.; de Matos Gomes, Etelvina; Castro, M. Cidália R.; Machado, Ana V.; Belsley, Michael S.; CrystEngComm 27 (2025) 2195–2203; doi:10.1039/D5CE00134J

data_7250083
_publ_section_title
;
 Second harmonic generation and crystal structure of a self-assembled
 Boc-p-nitro-l-phenylalanyl-p-nitro-l-phenylalanine dipeptide
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2195
_journal_page_last               2203
_journal_paper_doi               10.1039/D5CE00134J
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 N4 O9'
_chemical_formula_sum            'C23 H26 N4 O9'
_chemical_formula_weight         502.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_Hall           'P 2y'
_space_group_name_H-M_alt        'P 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-17
_audit_creation_method
;FinalCif V144 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-10-18 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.4730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4892(3)
_cell_length_b                   5.11310(10)
_cell_length_c                   18.7509(4)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      71.683
_cell_measurement_theta_min      3.539
_cell_volume                     1197.36(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'APEX 4 (2019) Bruker AXS Inc., Madison, WI 53719-1173'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'Bruker PHOTON II CPAD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52422
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.243
_diffrn_reflns_theta_min         3.539
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.40
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms HB'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.8149.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0357
_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/[\s^2^(Fo^2^)+(0.0467P)^2^+0.3854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4218
_reflns_number_total             4670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00134j2.cif
_cod_data_source_block           boc_pnphe_pnphe
_cod_depositor_comments          'Adding full bibliography for 7250083.cif.'
_cod_database_code               7250083
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C5(H5A), C6(H6), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.d Tetrahedral OH refined with riding coordinates:
 O5(H5)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.686
_shelx_estimated_absorpt_t_max   0.976
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              12364