Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones.
Diaba, Faïza; Montiel, Juan A.; Serban, Georgeta; Bonjoch, Josep; Organic letters 17 (2015) 3860–3863; doi:10.1021/acs.orglett.5b01832

data_1529250
_publ_section_title
;
 Synthesis of Normorphans through an Efficient Intramolecular
 Carbamoylation of Ketones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3860
_journal_page_last               3863
_journal_paper_doi               10.1021/acs.orglett.5b01832
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H16 Cl N O2'
_chemical_formula_sum            'C16 H16 Cl N O2'
_chemical_formula_weight         289.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9657(2)
_cell_length_b                   14.5166(3)
_cell_length_c                   12.0126(3)
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.81
_cell_volume                     1389.08(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4291
_diffrn_reflns_point_group_measured_fraction_full 0.756
_diffrn_reflns_point_group_measured_fraction_max 0.736
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_min         2.201
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.224
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0773P)^2^+0.5554P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.419
_reflns_Friedel_fraction_full    0.487
_reflns_Friedel_fraction_max     0.455
_reflns_number_gt                3026
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01832_si_003.cif
_cod_data_source_block           mo_D43TB83_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1529249--1529250.cif.'
_cod_database_code               1529250