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_7158121
_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         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_melting_point          333
_chemical_name_systematic        '2--Methoxyethyl quinolin--2--ylcarbamate'
_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   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                 95.9570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9095(2)
_cell_length_b                   7.96230(10)
_cell_length_c                   25.3411(4)
_cell_measurement_reflns_used    18983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1150
_cell_measurement_theta_min      4.2650
_cell_volume                     2390.04(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_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    -26.00  -1.00   0.50    3.26    --   47.20 -15.00  59.00   50
  2  \w     35.00 102.00   0.50   13.03    --  107.75 -77.00 150.00  134
  3  \w     62.00 126.00   0.50   13.03    --  107.75-144.00  43.78  128
  4  \w     77.00 118.00   0.50   13.03    --  107.75-133.00   9.18   82
  5  \w     81.00 106.00   0.50   13.03    --  107.75 -94.00-120.00   50
  6  \w     50.00 108.00   0.50   13.03    --  107.75-125.00 -90.00  116
  7  \w     39.00  95.00   0.50    3.26    --   47.20-125.00-120.00  112
  8  \w     39.00  77.00   0.50   13.03    --  107.75 -94.00-120.00   76
  9  \w     46.00 106.00   0.50   13.03    --  107.75 -77.00-120.00  120
 10  \w     41.00 121.00   0.50    3.26    --   47.20  15.00-129.00  160
 11  \w     94.00 175.00   0.50   13.03    --  107.75  15.00-129.00  162
 12  \w    120.00 175.00   0.50   13.03    --  107.75  45.00-120.00  110
 13  \w     44.00  70.00   0.50   13.03    --  107.75 -61.00  60.00   52
 14  \w     44.00  70.00   0.50   13.03    --  107.75 -61.00  90.00   52
 15  \w    100.00 178.00   0.50   13.03    --  107.75  15.00 150.00  156
 16  \w     46.00  74.00   0.50   13.03    --  107.75-133.00   9.18   56
 17  \w     50.00  75.00   0.50   13.03    --  107.75-125.00-120.00   50
 18  \w     35.00  71.00   0.50   13.03    --  107.75 -61.00-180.00   72
 19  \w     39.00  69.00   0.50   13.03    --  107.75 -61.00-120.00   60
 20  \w    -23.00  20.00   0.50    3.26    --  -47.20  15.00-129.00   86
 21  \w    -24.00  19.00   0.50    3.26    --  -47.20  37.00   0.00   86
 22  \w    -59.00 -34.00   0.50   13.03    -- -106.00  61.00  90.00   50
 23  \w    -81.00 -51.00   0.50   13.03    -- -106.00  77.00  30.00   60
 24  \w    -70.00 -35.00   0.50   13.03    -- -106.00  61.00 -30.00   70
 25  \w    -75.00 -34.00   0.50   13.03    -- -106.00 125.00-120.00   82
 26  \w   -112.00 -87.00   0.50   13.03    -- -106.00 125.00 -90.00   50
 27  \w   -120.00 -93.00   0.50   13.03    -- -106.00 137.00 -97.95   54
 28  \w   -114.00 -46.00   0.50    3.26    --  -47.20 -15.00  59.00  136
 29  \w   -124.00 -98.00   0.50   13.03    -- -106.00 -77.00 -30.00   52
 30  \w   -151.00-126.00   0.50   13.03    -- -106.00 -15.00  59.00   50
 31  \w     -7.00  19.00   0.50    3.26    --   47.20 -15.00  59.00   52
 32  \w    -55.00 -29.00   0.50    3.26    --  -47.20 -77.00 -30.00   52
 33  \w     42.00  68.00   0.50    3.26    --   47.20  57.00  60.00   52
 34  \w     41.00  68.00   0.50    3.26    --   47.20  19.00 -30.00   54
 35  \w     25.00  89.00   0.50    3.26    --   47.20  77.00 -60.00  128
 36  \w     33.00  58.00   0.50    3.26    --   47.20  57.00 -60.00   50
 37  \w     37.00  73.00   0.50    3.26    --   47.20  37.00 -30.00   72
 38  \w     29.00  55.00   0.50    3.26    --   47.20  77.00 -90.00   52
 39  \w     32.00  75.00   0.50    3.26    --   47.20  57.00  30.00   86
 40  \w   -110.00 -85.00   0.50   13.03    -- -106.00 -74.00  18.15   50
 41  \w   -116.00 -89.00   0.50   13.03    -- -106.00 -63.00  -2.51   54
 42  \w   -120.00 -87.00   0.50   13.03    -- -106.00 -68.00 -76.30   66
 43  \w   -116.00 -90.00   0.50   13.03    -- -106.00 -70.00 -49.59   52
 44  \w   -127.00 -86.00   0.50   13.03    -- -106.00 -70.00 -55.85   82
 45  \w   -159.00 -88.00   0.50   13.03    -- -106.00 -64.00 -10.21  142
 46  \w   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00   0.00   50
 47  \w   -107.00 -81.00   0.50   13.03    -- -106.00 -84.00 -75.69   52
 48  \w   -108.00 -83.00   0.50   13.03    -- -106.00 -77.00 -60.00   50
 49  \w   -171.00-146.00   0.50   13.03    -- -106.00 -81.00  54.00   50
 50  \w   -108.00 -83.00   0.50   13.03    -- -106.00 -77.00 -80.85   50
 51  \w   -111.00 -86.00   0.50   13.03    -- -106.00 -69.00 -20.90   50
 52  \w   -115.00 -81.00   0.50   13.03    -- -106.00 -81.00  54.00   68
 53  \w   -109.00 -81.00   0.50   13.03    -- -106.00 -82.00 -88.49   56
 54  \w   -155.00-130.00   0.50   13.03    -- -106.00 -82.00-106.78   50
 55  \w   -168.00-142.00   0.50   13.03    -- -106.00 -77.00  30.00   52
 56  \w   -116.00 -83.00   0.50   13.03    -- -106.00 -77.00  30.00   66
 57  \w   -163.00-137.00   0.50   13.03    -- -106.00 -70.00 -55.85   52
 58  \w   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00 -60.00   50
 59  \w   -146.00 -83.00   0.50   13.03    -- -106.00 -78.00  37.65  126
 60  \w   -151.00-125.00   0.50   13.03    -- -106.00 -45.00 -30.00   52
 61  \w   -109.00 -83.00   0.50   13.03    -- -106.00 -77.00 -90.00   52
 62  \w   -119.00 -89.00   0.50   13.03    -- -106.00 -61.00 -90.00   60
 63  \w    -68.00 -42.00   0.50   13.03    -- -106.00  61.00 150.00   52
 64  \w   -109.00 -84.00   0.50   13.03    -- -106.00 -77.00   0.00   50
 65  \w   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00 -36.23   50
 66  \w   -176.00 -91.00   0.50   13.03    -- -106.00 -56.00 -30.48  170
 67  \w   -137.00 -93.00   0.50   13.03    -- -106.00 -49.00 -82.91   88
 68  \w   -168.00-142.00   0.50   13.03    -- -106.00 -77.00   0.00   52
 69  \w   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00 -57.03   50
 70  \w   -114.00 -89.00   0.50   13.03    -- -106.00 -62.00  -8.07   50
 71  \w   -175.00-147.00   0.50   13.03    -- -106.00 -68.00 -80.81   56
 72  \w   -113.00 -88.00   0.50   13.03    -- -106.00 -68.00 -80.81   50
 73  \w   -117.00 -87.00   0.50   13.03    -- -106.00 -68.00 -87.32   60
 74  \w   -136.00 -85.00   0.50   13.03    -- -106.00 -72.00  17.48  102
 75  \w   -161.00-135.00   0.50   13.03    -- -106.00 -77.00  60.00   52
 76  \w   -110.00 -84.00   0.50   13.03    -- -106.00 -77.00  60.00   52
 77  \w   -176.00-150.00   0.50   13.03    -- -106.00 -61.00 -36.23   52
 78  \w   -108.00 -83.00   0.50   13.03    -- -106.00 -77.00 -30.00   50
 79  \w   -106.00 -81.00   0.50   13.03    -- -106.00 -82.00-106.78   50
 80  \w   -122.00 -93.00   0.50   13.03    -- -106.00 -45.00  30.00   58
 81  \w   -164.00-138.00   0.50   13.03    -- -106.00 -82.00 -88.49   52
 82  \w   -118.00 -93.00   0.50   13.03    -- -106.00 -50.00 -52.98   50
 83  \w   -138.00 -93.00   0.50   13.03    -- -106.00 -51.00 -62.55   90
 84  \w   -115.00 -90.00   0.50   13.03    -- -106.00 -60.00 -45.51   50
 85  \w   -105.00 -80.00   0.50   13.03    -- -106.00 -90.00 -86.81   50
 86  \w   -115.00 -86.00   0.50   13.03    -- -106.00 -71.00  34.43   58
 87  \w    114.00 139.00   0.50   13.03    --  107.75  77.00 -60.00   50
 88  \w     85.00 111.00   0.50   13.03    --  107.75  77.00 -60.00   52
 89  \w     90.00 115.00   0.50   13.03    --  107.75  66.00  24.12   50
 90  \w     86.00 112.00   0.50   13.03    --  107.75  77.00   0.00   52
 91  \w     87.00 113.00   0.50   13.03    --  107.75  77.00 -90.00   52
 92  \w     95.00 121.00   0.50   13.03    --  107.75  77.00 -30.00   52
 93  \w     83.00 111.00   0.50   13.03    --  107.75  81.00-113.50   56
 94  \w     35.00  60.00   0.50   13.03    --  107.75 -61.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1268503000
_diffrn_orient_matrix_UB_12      -0.0336250000
_diffrn_orient_matrix_UB_13      -0.0143887000
_diffrn_orient_matrix_UB_21      0.0153859000
_diffrn_orient_matrix_UB_22      0.0204078000
_diffrn_orient_matrix_UB_23      -0.0592871000
_diffrn_orient_matrix_UB_31      0.0241695000
_diffrn_orient_matrix_UB_32      -0.1894253000
_diffrn_orient_matrix_UB_33      -0.0038535000
_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  0.0473
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            48959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.841
_diffrn_reflns_theta_min         3.507
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2-dichloroethane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.9359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4637
_reflns_number_total             4990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00783a2.cif
_cod_data_source_block           16831_ucm-26
_cod_depositor_comments
'Adding full bibliography for 7158119--7158123.cif.'
_cod_database_code               7158121
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H14 N2  O3 '
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.860
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C12A(H12A,H12B), C12(H12C,H12D), C11(H11C,H11D)
2.b Aromatic/amide H refined with riding coordinates:
 N2A(H2A), N2(H2), C4(H4), C9(H9), C3(H3), C8(H8), C6(H6), C9A(H9A), C3A(H3A),
 C7(H7), C6A(H6A), C4A(H4A), C8A(H8A), C7A(H7A)
2.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13(H13D,H13E,H13F)
;
_shelx_res_checksum              88619
_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 2.481
_oxdiff_exptl_absorpt_empirical_full_min 0.658