Deprotective Lossen rearrangement: a direct and general transformation of Nms-amides to unsymmetrical ureas.
Spieß, Philipp; Brześkiewicz, Jakub; Maulide, Nuno; Chemical science 15 (2024) 15799–15803; doi:10.1039/d4sc04974h

data_1572562
_publ_section_title
;
 Deprotective Lossen rearrangement: a direct and general transformation of
 Nms-amides to unsymmetrical ureas.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              15799
_journal_page_last               15803
_journal_paper_doi               10.1039/d4sc04974h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-11
_audit_creation_method           'STOE LANA'
_audit_update_record
;
2023-06-12 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.852(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.3525(12)
_cell_length_b                   8.6525(5)
_cell_length_c                   11.7801(8)
_cell_measurement_reflns_used    14561
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.39
_cell_measurement_theta_min      6.44
_cell_volume                     2093.6(2)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)
;
_computing_data_reduction
'  X-Area Integrate 2.5.3.0 (STOE, 2021)  X-Area LANA 2.7.5.0 (STOE, 2022)'
_computing_molecular_graphics    'ShelXle (H\"ubschle 2011)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.1, Darmstadt 2022
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      ' 6000 frames, detector distance = 40 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19219
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.588
_diffrn_reflns_theta_min         4.305
_diffrn_source                   'Primux 100 micro'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.7974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_size_rad          0.031
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0753P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1470
_reflns_d_resolution_high        0.828
_reflns_d_resolution_low         11.332
_reflns_Friedel_coverage         0.000
_reflns_limit_h_max              8
_reflns_limit_h_min              -14
_reflns_limit_k_max              6
_reflns_limit_k_min              -10
_reflns_limit_l_max              25
_reflns_limit_l_min              -24
_reflns_number_gt                2313
_reflns_number_total             3737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04974h2.cif
_cod_data_source_block           PHSP-1071_a
_cod_depositor_comments
;
Adding full bibliography for 1572561--1572562.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H24 N4 O4'
_cod_original_formula_weight         432.47
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2093.78(22)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572562
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'J. Richter'
_stoe_detector_size_x            '7.7 cm'
_stoe_detector_size_y            '3.8 cm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_distance          '40.0 mm'
_stoe_measurement_identifier     PHSP1071
_stoe_measurement_tube_power     '50.0 W'
_stoe_measurement_total_run_number 30
_stoe_measurement_total_frame_number 6000
_stoe_measurement_min_exposure_per_frame '10.0 s'
_stoe_measurement_max_exposure_per_frame '10.0 s'
_stoe_measurement_mean_exposure_per_frame '10.0 s'
_stoe_measurement_total_exposure_time '16.7 h'
_stoe_evaluation_integration_a   14.0
_stoe_evaluation_integration_b   1.0
_stoe_evaluation_integration_ems 0.050
_stoe_evaluation_lana_point_group 2/m
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_dxs_max_order -
_stoe_evaluation_lana_dys_max_order -
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_or_c1      0.050
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      1.0
_stoe_evaluation_lana_max_2theta_available 137.2
_stoe_evaluation_lana_max_2theta_desired 137.2
_stoe_evaluation_lana_number_refls_total 21436
_stoe_evaluation_lana_number_refls_outliers 1303
_stoe_evaluation_lana_number_refls_after_or 20133
_stoe_evaluation_lana_number_refls_unique 4012
_stoe_evaluation_lana_number_refls_written 20133
_stoe_evaluation_lana_completeness 96.6
_stoe_evaluation_lana_mean_redundancy 5.0
_stoe_evaluation_lana_table
;
2Theta          14.1   28.7   43.3   57.9   72.5   87.1  101.7  116.3  130.9
<Resolution>    5.38   3.01   2.07   1.56   1.30   1.12   1.00   0.91   0.85
N(total)         168    567    803   2866   4425   4155   3608   3124   1720
<Redundancy>     3.7    4.0    2.9    6.6    7.5    5.9    4.7    4.2    3.0
Complet. [%%]    97.5   99.3   99.2   99.8  100.0  100.0   98.4   95.4   85.3
<I/sigma>       63.2   50.4   17.7    8.2    4.7    4.1    3.0    1.8    1.5
R(int)         0.010  0.014  0.032  0.076  0.125  0.141  0.177  0.264  0.325
;
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.992
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              76056
_shelx_hkl_checksum              50015