Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols.
Kasatkina, Svetlana O.; Geyl, Kirill K.; Baykov, Sergey V.; Boyarskaya, Irina A.; Boyarskiy, Vadim P.; Organic & biomolecular chemistry 19 (2021) 6059–6065; doi:10.1039/d1ob00783a

data_7158119
_publ_section_title
;
 Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and
 isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and
 alcohols.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6059
_journal_page_last               6065
_journal_paper_doi               10.1039/d1ob00783a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C8 H10 N2 O2'
_chemical_formula_sum            'C8 H10 N2 O2'
_chemical_formula_weight         166.18
_chemical_melting_point          414
_chemical_name_systematic        'Methyl (4--methylpyridin--2--yl)carbamate'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2020-12-16 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.589(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9064(3)
_cell_length_b                   18.7809(8)
_cell_length_c                   7.4306(4)
_cell_measurement_reflns_used    1489
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7900
_cell_measurement_theta_min      4.6910
_cell_volume                     817.04(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_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      1.00  28.00   1.00    1.00    --  -40.13  38.00 -90.00   27
  2  \w    -67.00 -19.00   1.00    1.00    --  -40.13  38.00 -90.00   48
  3  \w   -109.00 -14.00   1.00    1.00    --  -40.13 -38.00  90.00   95
  4  \w     92.00 130.00   1.00    1.00    --   40.13 178.00  30.00   38
  5  \w    107.00 134.00   1.00    1.00    --  113.00 112.00 120.00   27
  6  \w    151.00 176.00   1.00    1.00    --  113.00 112.00 120.00   25
  7  \w     98.00 166.00   1.00    1.00    --  113.00  45.00  60.00   68
  8  \w     86.00 178.00   1.00    1.00    --  113.00  61.00   0.00   92
  9  \w    141.00 178.00   1.00    1.00    --  113.00 112.00-150.00   37
 10  \w    103.00 150.00   1.00    1.00    --  113.00 112.00-180.00   47
 11  \w     55.00 137.00   1.00    1.00    --  113.00 -61.00-150.00   82
 12  \w     71.00 109.00   1.00    1.00    --  113.00 -95.00-180.00   38
 13  \w     82.00 108.00   1.00    1.00    --   40.13-178.00 150.00   26
 14  \w     46.00 110.00   1.00    1.00    --  113.00-112.00 150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0308340000
_diffrn_orient_matrix_UB_12      -0.0791611000
_diffrn_orient_matrix_UB_13      0.0452230000
_diffrn_orient_matrix_UB_21      -0.1601477000
_diffrn_orient_matrix_UB_22      0.0209966000
_diffrn_orient_matrix_UB_23      0.1390290000
_diffrn_orient_matrix_UB_31      -0.2065037000
_diffrn_orient_matrix_UB_32      -0.0043955000
_diffrn_orient_matrix_UB_33      -0.1495906000
_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  0.0232
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3366
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.066
_diffrn_reflns_theta_min         4.709
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0695P)^2^+0.0757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1396
_reflns_number_total             1661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00783a2.cif
_cod_data_source_block           1ver0-13840_kkg-164
_cod_depositor_comments
'Adding full bibliography for 7158119--7158123.cif.'
_cod_database_code               7158119
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 H13 Cl2 N3 O1 Zn1'
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.866
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              28069
_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.485