Combining X-ray and NMR crystallography to explore the structural disorder in racemic propranolol hydrochloride
Szeleszczuk, Łukasz; Bethanis, Kostas; Christoforides, Elias; Pisklak, Dariusz Maciej; CrystEngComm 27 (2025) 433–446; doi:10.1039/D4CE01105H

data_7249723
_publ_section_title
;
 Combining X-ray and NMR crystallography to explore the structural
 disorder in racemic propranolol hydrochloride
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              433
_journal_page_last               446
_journal_paper_doi               10.1039/D4CE01105H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C16 H22 N O2, Cl'
_chemical_formula_sum            'C16 H22 Cl N O2'
_chemical_formula_weight         295.79
_chemical_name_common            PropranololHCI
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-10-25 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.530(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7680(4)
_cell_length_b                   8.2450(2)
_cell_length_c                   13.9478(4)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.1263
_cell_measurement_theta_min      4.2107
_cell_volume                     1565.80(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker, D8-VENTURE'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_min         4.210
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0865 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.9118.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0327P)^2^+0.7922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             2860
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {5504f69c-001d-4a34-ad44-2261e71722dc}
_cod_data_source_file            d4ce01105h2.cif
_cod_data_source_block           cu_2023kb001_0m
_cod_depositor_comments          'Adding full bibliography for 7249723.cif.'
_cod_database_code               7249723
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.918
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C16-O1 \\sim C16-O1A
 with sigma of 0.02
3. Others
 Fixed Sof: H16(0.5) H16A(0.5) O1(0.5) H1C(0.5) O1A(0.5) H1AA(0.5)
4.a Ternary CH refined with riding coordinates:
 C16(H16), C16(H16A), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C9(H9), C10(H10), C1(H1), C3(H3), C2(H2)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1C), O1A(H1AA)
;
_shelx_res_checksum              73866