Zinc catalyzed chemoselective hydrofunctionalization of cyanamides.
Rajput, Sagrika; Sahoo, Rajata Kumar; M T, Nithya; Nembenna, Sharanappa; Chemical communications (Cambridge, England) 60 (2024) 11148–11151; doi:10.1039/d4cc03972f

data_7133723
_publ_section_title
;
 Zinc catalyzed chemoselective hydrofunctionalization of cyanamides.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11148
_journal_page_last               11151
_journal_paper_doi               10.1039/d4cc03972f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13 H27 B N2 O2'
_chemical_formula_sum            'C13 H27 B N2 O2'
_chemical_formula_weight         254.17
_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     iterative
_audit_creation_date             2024-05-20
_audit_creation_method
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_audit_update_record
;
2024-05-22 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.667(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.11292(18)
_cell_length_b                   19.9526(6)
_cell_length_c                   12.9873(4)
_cell_measurement_reflns_used    9504
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5220
_cell_measurement_theta_min      4.3980
_cell_volume                     1556.67(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac5-021 (Bourhis et al., 2015)'
_computing_structure_solution
'olex2.solve 1.5-ac5-021 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -85.00  -3.00   0.50    0.25    --  -38.50 121.00 179.00  164
  2  \w   -106.00 -20.00   0.50    0.25    --  -38.50 152.00 -20.00  172
  3  \w     42.00 118.00   0.50    0.25    --   49.06-152.00 -62.00  152
  4  \w     42.00 131.00   0.50    0.97    --  102.63-152.00 -62.00  178
  5  \w     99.00 167.00   0.50    0.97    --  102.63 121.00 179.00  136
  6  \w     81.00 165.00   0.50    0.97    --  102.63 152.00 -20.00  168
  7  \w     39.00 110.00   0.50    0.97    --  102.63-121.00  96.00  142
  8  \w    -44.00  31.00   0.50    0.25    --  -38.50  19.00 120.00  150
  9  \w   -101.00 -27.00   0.50    0.25    --  -38.50 -57.00-180.00  148
 10  \w    -17.00  52.00   0.50    0.25    --   49.06 -37.00  90.00  138
 11  \w     98.00 167.00   0.50    0.97    --  102.63  45.00-180.00  138
 12  \w     97.00 166.00   0.50    0.97    --  102.63 125.00 -60.00  138
 13  \w     38.00 107.00   0.50    0.97    --  102.63 -45.00-150.00  138
 14  \w     35.00 106.00   0.50    0.97    --  102.63 -30.00-150.00  142
 15  \w     40.00 112.00   0.50    0.97    --  102.63-125.00 150.00  144
 16  \w    103.00 167.00   0.50    0.97    --  102.63  77.00-120.00  128
 17  \w     40.00 116.00   0.50    0.97    --  102.63 -61.00  60.00  152
 18  \w    103.00 167.00   0.50    0.97    --  102.63  77.00-180.00  128
 19  \w    105.00 130.00   0.50    0.97    --  102.63  77.00 -60.00   50
 20  \w     68.00 107.00   0.50    0.97    --  102.63 -45.00  60.00   78
 21  \w    128.00 165.00   0.50    0.97    --  102.63  61.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577178000
_diffrn_orient_matrix_UB_12      0.0568553000
_diffrn_orient_matrix_UB_13      0.0808706000
_diffrn_orient_matrix_UB_21      0.1009736000
_diffrn_orient_matrix_UB_22      -0.0515392000
_diffrn_orient_matrix_UB_23      0.0836789000
_diffrn_orient_matrix_UB_31      0.2286168000
_diffrn_orient_matrix_UB_32      0.0084463000
_diffrn_orient_matrix_UB_33      -0.0321328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         4.112
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0949P)^2^+1.8647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.2007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2707
_reflns_number_total             2840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03972f3.cif
_cod_data_source_block           sn_rks_c12_19_auto
_cod_depositor_comments
'Adding full bibliography for 7133723--7133724.cif.'
_cod_original_cell_volume        1556.66(8)
_cod_database_code               7133723
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O B'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.c Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C18(H18a,H18b,H18c), C7(H7a,H7b,H7c), C17(H17a,H17b,H17c),
 C16(H16a,H16b,H16c), C6(H6a,H6b,H6c), C4(H4a,H4b,H4c), C15(H15a,H15b,H15c)
;
_shelx_res_checksum              42217
_shelx_hkl_checksum              923
_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 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.523