nBu4NI-catalyzed oxidative cross-coupling of carbon dioxide, amines, and aryl ketones: access to O-β-oxoalkyl carbamates.
Peng, Youbin; Liu, Juan; Qi, Chaorong; Yuan, Gaoqing; Li, Jiawei; Jiang, Huanfeng; Chemical communications (Cambridge, England) 53 (2017) 2665–2668; doi:10.1039/c6cc09762f

data_7119439
_publ_section_title
;
 nBu4NI-catalyzed oxidative cross-coupling of carbon dioxide, amines, and
 aryl ketones: access to O-\b-oxoalkyl carbamates.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2665
_journal_page_last               2668
_journal_paper_doi               10.1039/c6cc09762f
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C14 H17 N O3 S'
_chemical_formula_sum            'C14 H17 N O3 S'
_chemical_formula_weight         279.35
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.0008(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.04588(15)
_cell_length_b                   9.57981(12)
_cell_length_c                   15.0463(2)
_cell_measurement_reflns_used    3814
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8600
_cell_measurement_theta_min      4.6700
_cell_volume                     1369.12(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -68.00  31.00   1.00    1.00    --  -41.89  57.00 120.00   99
  2  \w     57.00  89.00   1.00    1.00    --   41.89-125.00 -90.00   32
  3  \w     36.00 130.00   1.00    1.00    --  107.79 -45.00  30.00   94
  4  \w     76.00 138.00   1.00    1.00    --  107.79 -77.00 120.00   62
  5  \w    108.00 163.00   1.00    1.00    --  107.79  30.00 -90.00   55
  6  \w     95.00 124.00   1.00    1.00    --  107.79 125.00  30.00   29
  7  \w    137.00 177.00   1.00    1.00    --  107.79 125.00  30.00   40
  8  \w    128.00 164.00   1.00    1.00    --  107.79 125.00 120.00   36
  9  \w     80.00 169.00   1.00    1.00    --  107.79  77.00-180.00   89
 10  \w   -107.00 -19.00   1.00    1.00    --  -41.89 -57.00 -30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0415454000
_diffrn_orient_matrix_UB_12      -0.0144492000
_diffrn_orient_matrix_UB_13      0.0894906000
_diffrn_orient_matrix_UB_21      -0.1141744000
_diffrn_orient_matrix_UB_22      0.1125029000
_diffrn_orient_matrix_UB_23      -0.0374172000
_diffrn_orient_matrix_UB_31      -0.1073848000
_diffrn_orient_matrix_UB_32      -0.1140821000
_diffrn_orient_matrix_UB_33      -0.0481428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5057
_diffrn_reflns_theta_full        74.05
_diffrn_reflns_theta_max         74.05
_diffrn_reflns_theta_min         4.68
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.3759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                2536
_reflns_number_total             2703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc09762f2.cif
_cod_data_source_block           1606072
_cod_depositor_comments          'Adding full bibliography for 7119439.cif.'
_cod_original_cell_volume        1369.13(3)
_cod_database_code               7119439
_chemical_oxdiff_formula         'C12 H20 N2 O4 S'
_chemical_oxdiff_usercomment     pyb-160522-1
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.676