#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:51:44 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517576.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_4517576
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            'C18 H14 N2 O5'
_chemical_formula_weight         338.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                92.011(4)
_cell_angle_beta                 102.586(4)
_cell_angle_gamma                97.486(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4602(8)
_cell_length_b                   7.7802(9)
_cell_length_c                   14.1269(15)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      2.83
_cell_volume                     791.72(15)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29774
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.875
_diffrn_reflns_theta_min         2.826
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0546
_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)+(0.0415P)²+0.4570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3097
_reflns_number_total             4085
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00884_si_004.cif
_cod_data_source_block           A19077_002
_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_database_code               4517576
_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   0.965
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.48355(19) 0.25307(17) 0.15011(10) 0.0290(3) Uani 1 1 d . . . . .
C2 C 0.5316(3) 0.0770(2) 0.13890(14) 0.0388(4) Uani 1 1 d . . . . .
H2A H 0.661087 0.084396 0.131148 0.047 Uiso 1 1 calc R U . . .
H2AB H 0.448987 0.014406 0.079968 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5112(3) -0.0195(2) 0.22583(15) 0.0417(5) Uani 1 1 d . . . . .
H3 H 0.482296 -0.142511 0.219371 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5327(3) 0.0630(2) 0.31232(14) 0.0398(4) Uani 1 1 d . . . . .
H4 H 0.514238 -0.000503 0.366435 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5847(2) 0.2516(2) 0.32432(12) 0.0309(4) Uani 1 1 d . . . . .
C6 C 0.5658(2) 0.3458(2) 0.24091(11) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.6310(2) 0.5217(2) 0.24736(11) 0.0283(3) Uani 1 1 d . . . . .
H7 H 0.625803 0.582870 0.190026 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7038(2) 0.6079(2) 0.33745(12) 0.0302(4) Uani 1 1 d . . . . .
H8 H 0.745964 0.729156 0.341947 0.036 Uiso 1 1 calc R U . . .
C9 C 0.7155(2) 0.5187(2) 0.42129(12) 0.0322(4) Uani 1 1 d . . . . .
C10 C 0.6579(2) 0.3408(2) 0.41409(13) 0.0356(4) Uani 1 1 d . . . . .
H10 H 0.668757 0.279236 0.471485 0.043 Uiso 1 1 calc R U . . .
C11 C 0.7947(3) 0.6074(3) 0.51917(13) 0.0397(4) Uani 1 1 d . . . . .
O12 O 0.8180(3) 0.5352(2) 0.59307(10) 0.0657(5) Uani 1 1 d . . . . .
O13 O 0.8369(2) 0.7780(2) 0.51564(10) 0.0559(4) Uani 1 1 d . . . . .
C14 C 0.9177(4) 0.8752(3) 0.60747(16) 0.0634(7) Uani 1 1 d . . . . .
H14A H 0.956615 0.996360 0.595783 0.095 Uiso 1 1 calc R U . . .
H14B H 1.025712 0.824512 0.641227 0.095 Uiso 1 1 calc R U . . .
H14C H 0.825655 0.870668 0.647652 0.095 Uiso 1 1 calc R U . . .
C15 C 0.3622(2) 0.3127(2) 0.07527(11) 0.0273(3) Uani 1 1 d . . . . .
O16 O 0.32825(18) 0.24435(17) -0.00673(9) 0.0406(3) Uani 1 1 d . . . . .
C17 C 0.2658(2) 0.4614(2) 0.09784(11) 0.0251(3) Uani 1 1 d . . . . .
C18 C 0.2411(2) 0.5887(2) 0.03155(11) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.284726 0.579780 -0.026541 0.033 Uiso 1 1 calc R U . . .
C19 C 0.1536(2) 0.7278(2) 0.04957(11) 0.0285(3) Uani 1 1 d . . . . .
H19 H 0.139205 0.817089 0.005470 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0876(2) 0.7340(2) 0.13310(11) 0.0257(3) Uani 1 1 d . . . . .
C21 C 0.1010(2) 0.6055(2) 0.19796(11) 0.0275(3) Uani 1 1 d . . . . .
H21 H 0.049103 0.610957 0.253525 0.033 Uiso 1 1 calc R U . . .
C22 C 0.1924(2) 0.4685(2) 0.17987(11) 0.0278(3) Uani 1 1 d . . . . .
H22 H 0.204844 0.378766 0.223763 0.033 Uiso 1 1 calc R U . . .
N23 N 0.0055(2) 0.88734(18) 0.15652(10) 0.0314(3) Uani 1 1 d . . . . .
O24 O 0.0392(2) 1.01919(17) 0.11586(11) 0.0496(4) Uani 1 1 d . . . . .
O25 O -0.08831(19) 0.87713(18) 0.21693(10) 0.0444(3) Uani 1 1 d . . . . .
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
C15 N1 C6 125.39(13) . . ?
C15 N1 C2 118.82(14) . . ?
C6 N1 C2 115.76(13) . . ?
N1 C2 C3 109.78(15) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2AB 109.7 . . ?
C3 C2 H2AB 109.7 . . ?
H2A C2 H2AB 108.2 . . ?
C4 C3 C2 121.25(16) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.05(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C10 C5 C6 118.48(15) . . ?
C10 C5 C4 123.14(16) . . ?
C6 C5 C4 118.34(16) . . ?
C7 C6 C5 120.63(15) . . ?
C7 C6 N1 121.78(14) . . ?
C5 C6 N1 117.56(14) . . ?
C8 C7 C6 119.79(15) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.42(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.50(16) . . ?
C8 C9 C11 121.72(16) . . ?
C10 C9 C11 118.75(16) . . ?
C5 C10 C9 121.00(15) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
O12 C11 O13 123.23(18) . . ?
O12 C11 C9 124.44(19) . . ?
O13 C11 C9 112.34(15) . . ?
C11 O13 C14 116.34(17) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 C15 N1 121.50(15) . . ?
O16 C15 C17 120.44(14) . . ?
N1 C15 C17 118.02(13) . . ?
C22 C17 C18 119.93(14) . . ?
C22 C17 C15 121.47(14) . . ?
C18 C17 C15 118.49(14) . . ?
C19 C18 C17 120.37(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 118.24(14) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C19 C20 C21 122.95(14) . . ?
C19 C20 N23 118.77(14) . . ?
C21 C20 N23 118.24(14) . . ?
C20 C21 C22 118.11(14) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C17 120.27(14) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
O25 N23 O24 123.59(15) . . ?
O25 N23 C20 118.38(14) . . ?
O24 N23 C20 118.01(15) . . ?
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 C15 1.371(2) . ?
N1 C6 1.421(2) . ?
N1 C2 1.472(2) . ?
C2 C3 1.487(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.328(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.462(2) . ?
C4 H4 0.9500 . ?
C5 C10 1.388(2) . ?
C5 C6 1.400(2) . ?
C6 C7 1.384(2) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 C11 1.486(2) . ?
C10 H10 0.9500 . ?
C11 O12 1.193(2) . ?
C11 O13 1.329(2) . ?
O13 C14 1.446(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O16 1.2177(19) . ?
C15 C17 1.500(2) . ?
C17 C22 1.388(2) . ?
C17 C18 1.389(2) . ?
C18 C19 1.379(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(2) . ?
C20 N23 1.469(2) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N23 O25 1.2144(19) . ?
N23 O24 1.2176(19) . ?
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
C15 N1 C2 C3 -130.71(16) . . . . ?
C6 N1 C2 C3 47.6(2) . . . . ?
N1 C2 C3 C4 -28.1(2) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C3 C4 C5 C10 -161.94(18) . . . . ?
C3 C4 C5 C6 15.8(3) . . . . ?
C10 C5 C6 C7 4.6(2) . . . . ?
C4 C5 C6 C7 -173.17(16) . . . . ?
C10 C5 C6 N1 -177.49(15) . . . . ?
C4 C5 C6 N1 4.7(2) . . . . ?
C15 N1 C6 C7 -41.3(2) . . . . ?
C2 N1 C6 C7 140.45(16) . . . . ?
C15 N1 C6 C5 140.85(17) . . . . ?
C2 N1 C6 C5 -37.4(2) . . . . ?
C5 C6 C7 C8 -4.6(2) . . . . ?
N1 C6 C7 C8 177.64(15) . . . . ?
C6 C7 C8 C9 1.4(2) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C7 C8 C9 C11 179.39(16) . . . . ?
C6 C5 C10 C9 -1.6(3) . . . . ?
C4 C5 C10 C9 176.11(17) . . . . ?
C8 C9 C10 C5 -1.5(3) . . . . ?
C11 C9 C10 C5 -179.35(16) . . . . ?
C8 C9 C11 O12 -175.4(2) . . . . ?
C10 C9 C11 O12 2.4(3) . . . . ?
C8 C9 C11 O13 4.8(3) . . . . ?
C10 C9 C11 O13 -177.44(17) . . . . ?
O12 C11 O13 C14 1.1(3) . . . . ?
C9 C11 O13 C14 -179.07(18) . . . . ?
C6 N1 C15 O16 164.03(16) . . . . ?
C2 N1 C15 O16 -17.8(2) . . . . ?
C6 N1 C15 C17 -18.3(2) . . . . ?
C2 N1 C15 C17 159.94(15) . . . . ?
O16 C15 C17 C22 134.59(17) . . . . ?
N1 C15 C17 C22 -43.2(2) . . . . ?
O16 C15 C17 C18 -41.6(2) . . . . ?
N1 C15 C17 C18 140.67(15) . . . . ?
C22 C17 C18 C19 3.9(2) . . . . ?
C15 C17 C18 C19 -179.85(14) . . . . ?
C17 C18 C19 C20 -1.8(2) . . . . ?
C18 C19 C20 C21 -1.7(2) . . . . ?
C18 C19 C20 N23 175.86(14) . . . . ?
C19 C20 C21 C22 2.9(2) . . . . ?
N23 C20 C21 C22 -174.64(14) . . . . ?
C20 C21 C22 C17 -0.7(2) . . . . ?
C18 C17 C22 C21 -2.6(2) . . . . ?
C15 C17 C22 C21 -178.76(15) . . . . ?
C19 C20 N23 O25 163.94(15) . . . . ?
C21 C20 N23 O25 -18.4(2) . . . . ?
C19 C20 N23 O24 -17.8(2) . . . . ?
C21 C20 N23 O24 159.83(15) . . . . ?
