#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:51:44 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517578.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_4517578
loop_
_publ_author_name
'Jeong, Jinseong'
'Heo, Joon'
'Kim, Dongwook'
'Chang, Sukbok'
_publ_section_title
;
 NHC-Catalyzed 1,2-Selective Hydroboration of Quinolines
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              5023
_journal_page_last               5029
_journal_paper_doi               10.1021/acscatal.0c00884
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.5627(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5628(17)
_cell_length_b                   16.969(4)
_cell_length_c                   11.191(2)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.24
_cell_volume                     1383.5(5)
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_collection       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23515
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.099
_diffrn_reflns_theta_min         2.796
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.228
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0382
_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/[σ²(Fo²)+(0.0432P)²+0.5929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2841
_reflns_number_total             3354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00884_si_002.cif
_cod_data_source_block           A19040_014
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4517576--4517579.cif.

 Adding full bibliography for 4517576--4517579.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517578
_shelx_shelxl_version_number     2018/3
_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_min   0.966
_shelx_estimated_absorpt_t_max   0.978
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
N1 N 0.84310(14) 0.47160(5) 0.25673(9) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.86088(18) 0.52894(7) 0.16260(11) 0.0234(3) Uani 1 1 d . . . . .
H1A H 0.992441 0.539321 0.170885 0.028 Uiso 1 1 calc R U . . .
H1B H 0.802410 0.579222 0.175754 0.028 Uiso 1 1 calc R U . . .
C2 C 0.77153(16) 0.49841(7) 0.03462(11) 0.0225(2) Uani 1 1 d . . . . .
C3 C 0.76082(17) 0.42075(7) 0.01501(11) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.698526 0.401134 -0.064677 0.028 Uiso 1 1 calc R U . . .
C4 C 0.84349(16) 0.36556(7) 0.11427(11) 0.0198(2) Uani 1 1 d . . . . .
C5 C 0.89110(15) 0.39234(6) 0.23717(11) 0.0174(2) Uani 1 1 d . . . . .
C6 C 0.98637(16) 0.34422(7) 0.33317(11) 0.0206(2) Uani 1 1 d . . . . .
H6 H 1.022298 0.363545 0.415847 0.025 Uiso 1 1 calc R U . . .
C7 C 1.02885(17) 0.26741(7) 0.30732(12) 0.0245(3) Uani 1 1 d . . . . .
H7 H 1.092780 0.233993 0.372824 0.029 Uiso 1 1 calc R U . . .
C8 C 0.97854(18) 0.23937(7) 0.18675(13) 0.0268(3) Uani 1 1 d . . . . .
H8 H 1.006949 0.186746 0.169629 0.032 Uiso 1 1 calc R U . . .
C9 C 0.88673(17) 0.28827(7) 0.09126(12) 0.0243(3) Uani 1 1 d . . . . .
H9 H 0.852642 0.268787 0.008655 0.029 Uiso 1 1 calc R U . . .
C10 C 0.79226(15) 0.49882(7) 0.35727(10) 0.0183(2) Uani 1 1 d . . . . .
O1 O 0.80434(13) 0.56895(5) 0.38476(9) 0.0255(2) Uani 1 1 d . . . . .
C11 C 0.70851(15) 0.44322(6) 0.43091(11) 0.0176(2) Uani 1 1 d . . . . .
C12 C 0.59697(15) 0.38016(7) 0.37748(11) 0.0191(2) Uani 1 1 d . . . . .
H12 H 0.579038 0.368509 0.292023 0.023 Uiso 1 1 calc R U . . .
C13 C 0.51210(16) 0.33438(7) 0.44859(11) 0.0204(2) Uani 1 1 d . . . . .
H13 H 0.434924 0.291605 0.412806 0.024 Uiso 1 1 calc R U . . .
C14 C 0.54257(16) 0.35253(7) 0.57256(11) 0.0197(2) Uani 1 1 d . . . . .
C15 C 0.64887(16) 0.41567(7) 0.62728(11) 0.0210(2) Uani 1 1 d . . . . .
H15 H 0.665541 0.427250 0.712650 0.025 Uiso 1 1 calc R U . . .
C16 C 0.73050(16) 0.46167(7) 0.55516(11) 0.0200(2) Uani 1 1 d . . . . .
H16 H 0.801954 0.506096 0.590587 0.024 Uiso 1 1 calc R U . . .
N2 N 0.46256(15) 0.30185(6) 0.65089(10) 0.0261(2) Uani 1 1 d . . . . .
O2 O 0.49508(16) 0.31732(7) 0.76128(9) 0.0410(3) Uani 1 1 d . . . . .
O3 O 0.36870(16) 0.24621(6) 0.60247(10) 0.0406(3) Uani 1 1 d . . . . .
C17 C 0.7059(2) 0.55932(8) -0.06361(13) 0.0318(3) Uani 1 1 d . . . . .
H17A H 0.652420 0.533345 -0.143340 0.048 Uiso 1 1 calc R U . . .
H17B H 0.809490 0.592238 -0.069928 0.048 Uiso 1 1 calc R U . . .
H17C H 0.612736 0.592358 -0.042023 0.048 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C10 N1 C5 125.89(10) . . ?
C10 N1 C1 117.93(9) . . ?
C5 N1 C1 116.08(9) . . ?
N1 C1 C2 110.58(10) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C17 124.66(12) . . ?
C3 C2 C1 119.29(11) . . ?
C17 C2 C1 116.02(11) . . ?
C2 C3 C4 120.91(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C9 C4 C5 118.42(11) . . ?
C9 C4 C3 122.52(11) . . ?
C5 C4 C3 118.95(11) . . ?
C6 C5 C4 120.84(10) . . ?
C6 C5 N1 122.50(10) . . ?
C4 C5 N1 116.62(10) . . ?
C5 C6 C7 119.43(11) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.41(12) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.77(11) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 121.07(11) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O1 C10 N1 121.14(11) . . ?
O1 C10 C11 119.11(10) . . ?
N1 C10 C11 119.63(10) . . ?
C16 C11 C12 119.85(11) . . ?
C16 C11 C10 116.92(10) . . ?
C12 C11 C10 122.90(10) . . ?
C13 C12 C11 120.25(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 118.30(11) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 122.69(11) . . ?
C13 C14 N2 119.02(10) . . ?
C15 C14 N2 118.28(11) . . ?
C14 C15 C16 118.53(11) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 120.29(11) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O3 N2 O2 123.49(11) . . ?
O3 N2 C14 118.20(11) . . ?
O2 N2 C14 118.30(11) . . ?
C2 C17 H17A 109.5 . . ?
C2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N1 C10 1.3636(15) . ?
N1 C5 1.4252(14) . ?
N1 C1 1.4665(15) . ?
C1 C2 1.5023(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3349(18) . ?
C2 C17 1.4935(17) . ?
C3 C4 1.4591(17) . ?
C3 H3 0.9500 . ?
C4 C9 1.3924(17) . ?
C4 C5 1.4007(16) . ?
C5 C6 1.3875(16) . ?
C6 C7 1.3912(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3843(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3835(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.2265(14) . ?
C10 C11 1.5002(16) . ?
C11 C16 1.3910(16) . ?
C11 C12 1.3941(16) . ?
C12 C13 1.3867(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3788(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3803(16) . ?
C14 N2 1.4692(15) . ?
C15 C16 1.3817(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N2 O3 1.2176(15) . ?
N2 O2 1.2217(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C10 N1 C1 C2 -134.97(11) . . . . ?
C5 N1 C1 C2 48.39(14) . . . . ?
N1 C1 C2 C3 -27.84(16) . . . . ?
N1 C1 C2 C17 154.19(11) . . . . ?
C17 C2 C3 C4 174.36(12) . . . . ?
C1 C2 C3 C4 -3.43(18) . . . . ?
C2 C3 C4 C9 -159.43(12) . . . . ?
C2 C3 C4 C5 16.81(17) . . . . ?
C9 C4 C5 C6 2.85(17) . . . . ?
C3 C4 C5 C6 -173.54(10) . . . . ?
C9 C4 C5 N1 -179.53(10) . . . . ?
C3 C4 C5 N1 4.08(15) . . . . ?
C10 N1 C5 C6 -36.15(17) . . . . ?
C1 N1 C5 C6 140.19(11) . . . . ?
C10 N1 C5 C4 146.27(11) . . . . ?
C1 N1 C5 C4 -37.39(14) . . . . ?
C4 C5 C6 C7 -2.46(17) . . . . ?
N1 C5 C6 C7 -179.94(10) . . . . ?
C5 C6 C7 C8 0.75(18) . . . . ?
C6 C7 C8 C9 0.52(18) . . . . ?
C7 C8 C9 C4 -0.09(18) . . . . ?
C5 C4 C9 C8 -1.57(17) . . . . ?
C3 C4 C9 C8 174.69(11) . . . . ?
C5 N1 C10 O1 158.72(11) . . . . ?
C1 N1 C10 O1 -17.56(17) . . . . ?
C5 N1 C10 C11 -25.35(17) . . . . ?
C1 N1 C10 C11 158.37(10) . . . . ?
O1 C10 C11 C16 -30.65(16) . . . . ?
N1 C10 C11 C16 153.34(11) . . . . ?
O1 C10 C11 C12 142.76(12) . . . . ?
N1 C10 C11 C12 -33.25(16) . . . . ?
C16 C11 C12 C13 -1.85(17) . . . . ?
C10 C11 C12 C13 -175.07(10) . . . . ?
C11 C12 C13 C14 -0.60(17) . . . . ?
C12 C13 C14 C15 2.14(18) . . . . ?
C12 C13 C14 N2 -176.44(10) . . . . ?
C13 C14 C15 C16 -1.15(18) . . . . ?
N2 C14 C15 C16 177.45(10) . . . . ?
C14 C15 C16 C11 -1.40(17) . . . . ?
C12 C11 C16 C15 2.87(17) . . . . ?
C10 C11 C16 C15 176.49(10) . . . . ?
C13 C14 N2 O3 -1.41(17) . . . . ?
C15 C14 N2 O3 179.95(12) . . . . ?
C13 C14 N2 O2 177.92(12) . . . . ?
C15 C14 N2 O2 -0.73(17) . . . . ?
