#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:51:44 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517579.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_4517579
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            'C16 H11 Cl N2 O3'
_chemical_formula_weight         314.72
_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                 106.556(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4538(3)
_cell_length_b                   16.3766(7)
_cell_length_c                   12.0863(5)
_cell_measurement_reflns_used    9189
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.49
_cell_volume                     1414.18(10)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.792
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       rod
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.203
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0397
_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)+(0.0424P)²+0.7697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2981
_reflns_number_total             3685
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00884_si_003.cif
_cod_data_source_block           A19041_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               4517579
_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   0.901
_shelx_estimated_absorpt_t_max   0.945
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 0.16991(16) 0.49567(7) 0.75108(10) 0.0220(2) Uani 1 1 d . . . . .
C1 C 0.1509(2) 0.56142(9) 0.83000(14) 0.0292(3) Uani 1 1 d . . . . .
H1A H 0.016829 0.574122 0.818017 0.035 Uiso 1 1 calc R U . . .
H1B H 0.213881 0.611386 0.813905 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2375(2) 0.53483(10) 0.95227(14) 0.0326(4) Uani 1 1 d . . . . .
H2 H 0.290660 0.574104 1.010182 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2397(2) 0.45636(10) 0.97927(13) 0.0296(3) Uani 1 1 d . . . . .
C4 C 0.1528(2) 0.39427(9) 0.89365(13) 0.0249(3) Uani 1 1 d . . . . .
C5 C 0.11571(19) 0.41598(8) 0.77663(12) 0.0214(3) Uani 1 1 d . . . . .
C6 C 0.0249(2) 0.36139(9) 0.69093(14) 0.0259(3) Uani 1 1 d . . . . .
H6 H -0.004060 0.376733 0.611997 0.031 Uiso 1 1 calc R U . . .
C7 C -0.0235(2) 0.28413(9) 0.72108(16) 0.0330(4) Uani 1 1 d . . . . .
H7 H -0.081757 0.246214 0.662344 0.040 Uiso 1 1 calc R U . . .
C8 C 0.0126(2) 0.26214(10) 0.83575(17) 0.0369(4) Uani 1 1 d . . . . .
H8 H -0.022785 0.209643 0.855632 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1002(2) 0.31672(10) 0.92153(15) 0.0335(4) Uani 1 1 d . . . . .
H9 H 0.124888 0.301332 1.000239 0.040 Uiso 1 1 calc R U . . .
C10 C 0.22841(19) 0.51645(8) 0.65700(12) 0.0229(3) Uani 1 1 d . . . . .
O1 O 0.22435(17) 0.58734(6) 0.62391(11) 0.0354(3) Uani 1 1 d . . . . .
C11 C 0.30773(19) 0.45091(8) 0.59772(12) 0.0205(3) Uani 1 1 d . . . . .
C12 C 0.42364(19) 0.38941(9) 0.65898(12) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.450897 0.386885 0.740629 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4993(2) 0.33183(9) 0.60069(12) 0.0240(3) Uani 1 1 d . . . . .
H13 H 0.578517 0.289666 0.641450 0.029 Uiso 1 1 calc R U . . .
C14 C 0.45643(19) 0.33741(8) 0.48208(12) 0.0228(3) Uani 1 1 d . . . . .
C15 C 0.3449(2) 0.39845(10) 0.41960(12) 0.0274(3) Uani 1 1 d . . . . .
H15 H 0.318793 0.400849 0.338011 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2720(2) 0.45609(9) 0.47849(13) 0.0266(3) Uani 1 1 d . . . . .
H16 H 0.197226 0.499381 0.437368 0.032 Uiso 1 1 calc R U . . .
N2 N 0.53034(19) 0.27502(8) 0.41905(11) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.4782(2) 0.27646(8) 0.31382(10) 0.0455(3) Uani 1 1 d . . . . .
O3 O 0.6388(2) 0.22415(8) 0.47497(12) 0.0492(4) Uani 1 1 d . . . . .
Cl1 Cl 0.34517(6) 0.42172(3) 1.12037(3) 0.04491(14) 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'
Cl Cl 0.1484 0.1585 '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 125.68(11) . . ?
C10 N1 C1 117.90(11) . . ?
C5 N1 C1 116.34(11) . . ?
N1 C1 C2 109.42(12) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C1 119.75(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.86(15) . . ?
C2 C3 Cl1 121.55(13) . . ?
C4 C3 Cl1 116.59(12) . . ?
C9 C4 C5 118.90(14) . . ?
C9 C4 C3 123.96(14) . . ?
C5 C4 C3 117.11(13) . . ?
C6 C5 C4 120.08(13) . . ?
C6 C5 N1 122.37(13) . . ?
C4 C5 N1 117.53(12) . . ?
C5 C6 C7 119.80(15) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.55(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.90(14) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.73(15) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
O1 C10 N1 121.43(13) . . ?
O1 C10 C11 119.85(13) . . ?
N1 C10 C11 118.65(12) . . ?
C16 C11 C12 120.05(13) . . ?
C16 C11 C10 117.72(12) . . ?
C12 C11 C10 122.10(12) . . ?
C13 C12 C11 120.04(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 118.33(13) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C14 C13 122.80(13) . . ?
C15 C14 N2 118.41(13) . . ?
C13 C14 N2 118.79(13) . . ?
C14 C15 C16 118.47(13) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 120.26(13) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O2 N2 O3 123.64(14) . . ?
O2 N2 C14 118.11(13) . . ?
O3 N2 C14 118.24(13) . . ?
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 1.3717(18) . ?
N1 C5 1.4259(17) . ?
N1 C1 1.4718(18) . ?
C1 C2 1.499(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.325(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.464(2) . ?
C3 Cl1 1.7561(16) . ?
C4 C9 1.399(2) . ?
C4 C5 1.407(2) . ?
C5 C6 1.389(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.2254(17) . ?
C10 C11 1.5021(19) . ?
C11 C16 1.391(2) . ?
C11 C12 1.3945(19) . ?
C12 C13 1.3892(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(2) . ?
C14 N2 1.4722(18) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N2 O2 1.2196(18) . ?
N2 O3 1.2218(18) . ?
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 -134.52(13) . . . . ?
C5 N1 C1 C2 48.70(16) . . . . ?
N1 C1 C2 C3 -29.7(2) . . . . ?
C1 C2 C3 C4 -2.5(2) . . . . ?
C1 C2 C3 Cl1 178.21(11) . . . . ?
C2 C3 C4 C9 -159.72(15) . . . . ?
Cl1 C3 C4 C9 19.62(19) . . . . ?
C2 C3 C4 C5 18.2(2) . . . . ?
Cl1 C3 C4 C5 -162.47(10) . . . . ?
C9 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C6 -176.77(13) . . . . ?
C9 C4 C5 N1 179.58(12) . . . . ?
C3 C4 C5 N1 1.56(18) . . . . ?
C10 N1 C5 C6 -34.1(2) . . . . ?
C1 N1 C5 C6 142.41(14) . . . . ?
C10 N1 C5 C4 147.63(14) . . . . ?
C1 N1 C5 C4 -35.87(17) . . . . ?
C4 C5 C6 C7 -2.2(2) . . . . ?
N1 C5 C6 C7 179.55(13) . . . . ?
C5 C6 C7 C8 2.1(2) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C5 C4 C9 C8 -0.2(2) . . . . ?
C3 C4 C9 C8 177.68(15) . . . . ?
C5 N1 C10 O1 160.05(14) . . . . ?
C1 N1 C10 O1 -16.4(2) . . . . ?
C5 N1 C10 C11 -23.0(2) . . . . ?
C1 N1 C10 C11 160.53(13) . . . . ?
O1 C10 C11 C16 -37.8(2) . . . . ?
N1 C10 C11 C16 145.27(14) . . . . ?
O1 C10 C11 C12 138.11(15) . . . . ?
N1 C10 C11 C12 -38.9(2) . . . . ?
C16 C11 C12 C13 -1.8(2) . . . . ?
C10 C11 C12 C13 -177.62(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 1.2(2) . . . . ?
C12 C13 C14 N2 -177.84(13) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
N2 C14 C15 C16 178.60(13) . . . . ?
C14 C15 C16 C11 -1.5(2) . . . . ?
C12 C11 C16 C15 2.6(2) . . . . ?
C10 C11 C16 C15 178.58(13) . . . . ?
C15 C14 N2 O2 -5.5(2) . . . . ?
C13 C14 N2 O2 173.67(14) . . . . ?
C15 C14 N2 O3 175.33(15) . . . . ?
C13 C14 N2 O3 -5.5(2) . . . . ?
