#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:26:01 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268923 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158119.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158119
loop_
_publ_author_name
'Kasatkina, Svetlana O.'
'Geyl, Kirill K.'
'Baykov, Sergey V.'
'Boyarskaya, Irina A.'
'Boyarskiy, Vadim P.'
_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 & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  28.00   1.00    1.00    --  -40.13  38.00 -90.00   27
  2  ω    -67.00 -19.00   1.00    1.00    --  -40.13  38.00 -90.00   48
  3  ω   -109.00 -14.00   1.00    1.00    --  -40.13 -38.00  90.00   95
  4  ω     92.00 130.00   1.00    1.00    --   40.13 178.00  30.00   38
  5  ω    107.00 134.00   1.00    1.00    --  113.00 112.00 120.00   27
  6  ω    151.00 176.00   1.00    1.00    --  113.00 112.00 120.00   25
  7  ω     98.00 166.00   1.00    1.00    --  113.00  45.00  60.00   68
  8  ω     86.00 178.00   1.00    1.00    --  113.00  61.00   0.00   92
  9  ω    141.00 178.00   1.00    1.00    --  113.00 112.00-150.00   37
 10  ω    103.00 150.00   1.00    1.00    --  113.00 112.00-180.00   47
 11  ω     55.00 137.00   1.00    1.00    --  113.00 -61.00-150.00   82
 12  ω     71.00 109.00   1.00    1.00    --  113.00 -95.00-180.00   38
 13  ω     82.00 108.00   1.00    1.00    --   40.13-178.00 150.00   26
 14  ω     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       'ω 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/[σ²(Fo²)+(0.0695P)²+0.0757P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.03982(16) 0.50191(5) 0.75347(15) 0.0211(3) Uani 1 1 d . . . . .
O1 O 1.02619(17) 0.62118(5) 0.79098(15) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.7447(2) 0.55967(6) 0.60923(16) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.705350 0.516169 0.573851 0.022 Uiso 1 1 calc R U . . .
N1 N 0.39338(19) 0.59146(6) 0.46363(16) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.5971(2) 0.61470(7) 0.54359(18) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.9445(2) 0.56722(7) 0.72326(19) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.6556(2) 0.68665(7) 0.55801(19) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.804026 0.700708 0.611075 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4939(2) 0.73746(8) 0.49373(18) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.2400(2) 0.64120(8) 0.4004(2) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.095014 0.625664 0.343275 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2801(2) 0.71380(8) 0.4134(2) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.164415 0.746839 0.368596 0.024 Uiso 1 1 calc R U . . .
C8 C 1.2551(2) 0.50200(8) 0.8700(2) 0.0230(3) Uani 1 1 d . . . . .
H8A H 1.369703 0.526958 0.809512 0.035 Uiso 1 1 calc R U . . .
H8B H 1.304642 0.452830 0.895705 0.035 Uiso 1 1 calc R U . . .
H8C H 1.237283 0.526287 0.984014 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5505(2) 0.81519(7) 0.5117(2) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.563211 0.829078 0.639810 0.032 Uiso 1 1 calc R U . . .
H7B H 0.429435 0.843040 0.441296 0.032 Uiso 1 1 calc R U . . .
H7C H 0.696006 0.824236 0.465901 0.032 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C8 114.38(11) . . ?
C2 N2 H2 117.0 . . ?
C1 N2 H2 117.0 . . ?
C1 N2 C2 125.97(12) . . ?
C6 N1 C2 116.91(12) . . ?
N1 C2 N2 113.28(12) . . ?
N1 C2 C3 123.17(13) . . ?
C3 C2 N2 123.55(12) . . ?
O2 C1 N2 108.33(12) . . ?
O1 C1 O2 123.88(12) . . ?
O1 C1 N2 127.77(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.13(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.05(13) . . ?
C3 C4 C7 120.18(13) . . ?
C5 C4 C7 121.77(13) . . ?
N1 C6 H6 118.0 . . ?
N1 C6 C5 124.01(13) . . ?
C5 C6 H6 118.0 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.67(13) . . ?
C6 C5 H5 120.7 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.3560(15) . ?
O2 C8 1.4405(16) . ?
O1 C1 1.2038(17) . ?
N2 H2 0.8800 . ?
N2 C2 1.3977(18) . ?
N2 C1 1.3660(18) . ?
N1 C2 1.3427(17) . ?
N1 C6 1.3424(18) . ?
C2 C3 1.3953(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.396(2) . ?
C4 C7 1.500(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C4 -177.87(13) . . . . ?
N1 C2 C3 C4 2.7(2) . . . . ?
N1 C6 C5 C4 1.3(2) . . . . ?
C2 N2 C1 O2 -179.13(12) . . . . ?
C2 N2 C1 O1 2.1(2) . . . . ?
C2 N1 C6 C5 -0.1(2) . . . . ?
C2 C3 C4 C5 -1.37(19) . . . . ?
C2 C3 C4 C7 178.50(12) . . . . ?
C1 N2 C2 N1 -167.67(13) . . . . ?
C1 N2 C2 C3 12.8(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C6 N1 C2 N2 178.60(12) . . . . ?
C6 N1 C2 C3 -1.9(2) . . . . ?
C8 O2 C1 O1 -2.2(2) . . . . ?
C8 O2 C1 N2 179.01(12) . . . . ?
C7 C4 C5 C6 179.65(13) . . . . ?
