#------------------------------------------------------------------------------
#$Date: 2020-12-19 00:15:50 +0200 (Sat, 19 Dec 2020) $
#$Revision: 259954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/83/4518328.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_4518328
loop_
_publ_author_name
'Nallagonda, Rajender'
'Karimov, Rashad R.'
_publ_section_title
;
 Copper-Catalyzed Regio- and Diastereoselective Additions of
 Boron-Stabilized Carbanions to Heteroarenium Salts: Synthesis of
 Azaheterocycles Containing Contiguous Stereocenters
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              248
_journal_page_last               254
_journal_paper_doi               10.1021/acscatal.0c04474
_journal_year                    2020
_chemical_formula_sum            'C26 H32 B0 N2 O4 S'
_chemical_formula_weight         468.59
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.1300(10)
_cell_angle_beta                 93.9170(10)
_cell_angle_gamma                90.8970(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2929(4)
_cell_length_b                   11.4055(5)
_cell_length_c                   12.1564(5)
_cell_measurement_reflns_used    9259
_cell_measurement_temperature    110.(2)
_cell_measurement_theta_max      74.6598
_cell_measurement_theta_min      4.7703
_cell_volume                     1245.86(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            59108
_diffrn_reflns_theta_full        74.69
_diffrn_reflns_theta_max         74.69
_diffrn_reflns_theta_min         4.00
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  0.58
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.430
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.382
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0360
_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)+(0.0404P)²+0.4744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                5029
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c04474_si_002.cif
_cod_data_source_block           Rajender052920
_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 
;
_cod_database_code               4518328
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.21845(4) 0.21529(3) 0.45527(3) 0.04363(12) Uani d . . . 1 . .
B B1 0.37359(13) 0.48083(11) 0.23864(10) 0.0214(2) Uani d . . . 1 . .
N N1 0.14883(10) 0.77083(9) 0.32074(8) 0.0253(2) Uani d . . . 1 . .
C C1 0.38194(18) 1.06092(13) 0.77966(12) 0.0428(3) Uani d . . . 1 . .
H H1A 0.339284 1.137824 0.775223 0.064 Uiso calc U . R 1 . .
H H1B 0.480062 1.076302 0.816108 0.064 Uiso calc U . R 1 . .
H H1C 0.323153 1.020752 0.824514 0.064 Uiso calc U . R 1 . .
O O1 0.38678(10) 0.98468(8) 0.66722(8) 0.0337(2) Uani d . . . 1 . .
O O2 0.14611(10) 1.00108(8) 0.64437(8) 0.0336(2) Uani d . . . 1 . .
C C2 0.25771(13) 0.96028(10) 0.60558(10) 0.0270(2) Uani d . . . 1 . .
O O3 0.49448(8) 0.46226(7) 0.30126(6) 0.02467(18) Uani d . . . 1 . .
C C3 0.27130(12) 0.88062(10) 0.49458(10) 0.0253(2) Uani d . . . 1 . .
C C6 0.40935(12) 0.75349(10) 0.35272(11) 0.0272(2) Uani d . . . 1 . .
H H6 0.499985 0.730751 0.323866 0.033 Uiso calc U . R 1 . .
C C5 0.27404(12) 0.69560(10) 0.28446(9) 0.0240(2) Uani d . . . 1 . .
H H5 0.285608 0.694419 0.203013 0.029 Uiso calc U . R 1 . .
O O4 0.37219(9) 0.42223(7) 0.12611(7) 0.02682(19) Uani d . . . 1 . .
C C4 0.14978(13) 0.84991(10) 0.42250(10) 0.0250(2) Uani d . . . 1 . .
H H4 0.061927 0.886285 0.445581 0.03 Uiso calc U . R 1 . .
C C7 0.40742(13) 0.83534(10) 0.45198(11) 0.0276(2) Uani d . . . 1 . .
H H7 0.495557 0.864201 0.49509 0.033 Uiso calc U . R 1 . .
C C8 0.02001(13) 0.75225(11) 0.24245(10) 0.0291(3) Uani d . . . 1 . .
H H8A -0.058592 0.800312 0.280206 0.035 Uiso calc U . R 1 . .
H H8B -0.011293 0.665867 0.224273 0.035 Uiso calc U . R 1 . .
C C9 0.04412(13) 0.78807(11) 0.13287(10) 0.0300(3) Uani d . . . 1 . .
C C13 -0.01481(18) 0.76178(18) -0.06837(12) 0.0534(4) Uani d . . . 1 . .
H H13 -0.06758 0.719685 -0.136651 0.064 Uiso calc U . R 1 . .
C C26 0.55730(16) 0.33257(13) 0.00295(11) 0.0387(3) Uani d . . . 1 . .
H H26A 0.485904 0.29841 -0.060384 0.058 Uiso calc U . R 1 . .
H H26B 0.641551 0.281406 -0.002509 0.058 Uiso calc U . R 1 . .
H H26C 0.587173 0.414313 -0.000453 0.058 Uiso calc U . R 1 . .
C C25 0.42383(15) 0.21578(11) 0.11507(13) 0.0380(3) Uani d . . . 1 . .
H H25A 0.38462 0.220021 0.188707 0.057 Uiso calc U . R 1 . .
H H25B 0.497589 0.154421 0.102112 0.057 Uiso calc U . R 1 . .
H H25C 0.345977 0.194028 0.054445 0.057 Uiso calc U . R 1 . .
C C24 0.49098(13) 0.33811(10) 0.11499(10) 0.0259(2) Uani d . . . 1 . .
C C23 0.70501(14) 0.48537(13) 0.20484(13) 0.0372(3) Uani d . . . 1 . .
H H23A 0.657561 0.542507 0.166856 0.056 Uiso calc U . R 1 . .
H H23B 0.778385 0.442797 0.15742 0.056 Uiso calc U . R 1 . .
H H23C 0.750974 0.529553 0.278585 0.056 Uiso calc U . R 1 . .
C C22 0.66479(14) 0.30229(12) 0.27830(11) 0.0320(3) Uani d . . . 1 . .
H H22A 0.728259 0.344441 0.344267 0.048 Uiso calc U . R 1 . .
H H22B 0.721741 0.248552 0.223357 0.048 Uiso calc U . R 1 . .
H H22C 0.590578 0.25448 0.303064 0.048 Uiso calc U . R 1 . .
C C21 0.59335(12) 0.39413(10) 0.22295(9) 0.0237(2) Uani d . . . 1 . .
C C20 0.06433(13) 0.36157(12) 0.37674(10) 0.0299(3) Uani d . . . 1 . .
H H20 -0.013974 0.395297 0.341944 0.036 Uiso calc U . R 1 . .
C C19 0.06140(14) 0.24643(13) 0.38874(11) 0.0358(3) Uani d . . . 1 . .
H H19 -0.017805 0.190461 0.36338 0.043 Uiso calc U . R 1 . .
C C18 0.28853(14) 0.35814(12) 0.46669(12) 0.0354(3) Uani d . . . 1 . .
H H18 0.381808 0.385738 0.501013 0.042 Uiso calc U . R 1 . .
C C17 0.19582(12) 0.42719(10) 0.42122(9) 0.0235(2) Uani d . . . 1 . .
C C16 0.22848(13) 0.55447(10) 0.41424(9) 0.0252(2) Uani d . . . 1 . .
H H16A 0.317893 0.585442 0.462288 0.03 Uiso calc U . R 1 . .
H H16B 0.148852 0.606455 0.44469 0.03 Uiso calc U . R 1 . .
C C15 0.24757(12) 0.56279(10) 0.29133(9) 0.0220(2) Uani d . . . 1 . .
H H15 0.156007 0.531485 0.244566 0.026 Uiso calc U . R 1 . .
C C14 -0.03068(16) 0.72641(15) 0.03196(12) 0.0430(3) Uani d . . . 1 . .
H H14 -0.093192 0.659546 0.031467 0.052 Uiso calc U . R 1 . .
C C12 0.07661(18) 0.85709(17) -0.06927(13) 0.0510(4) Uani d . . . 1 . .
H H12 0.087447 0.880818 -0.137999 0.061 Uiso calc U . R 1 . .
C C11 0.15299(18) 0.91854(14) 0.03044(13) 0.0453(4) Uani d . . . 1 . .
H H11 0.217011 0.984144 0.029964 0.054 Uiso calc U . R 1 . .
C C10 0.13629(15) 0.88448(12) 0.13144(12) 0.0358(3) Uani d . . . 1 . .
H H10 0.188287 0.9275 0.199743 0.043 Uiso calc U . R 1 . .
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'
B B 0.0090 0.0039 '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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 S1 C18 . . 91.78(6) ?
O3 B1 O4 . . 113.53(10) ?
O3 B1 C15 . . 123.07(10) ?
O4 B1 C15 . . 123.40(10) ?
C4 N1 C8 . . 120.35(9) ?
C4 N1 C5 . . 122.45(10) ?
C8 N1 C5 . . 117.16(9) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 O1 C1 . . 115.39(10) ?
O2 C2 O1 . . 121.60(11) ?
O2 C2 C3 . . 126.42(11) ?
O1 C2 C3 . . 111.96(10) ?
B1 O3 C21 . . 107.83(8) ?
C4 C3 C2 . . 118.28(10) ?
C4 C3 C7 . . 117.41(10) ?
C2 C3 C7 . . 124.23(11) ?
C7 C6 C5 . . 122.85(10) ?
C7 C6 H6 . . 118.6 ?
C5 C6 H6 . . 118.6 ?
N1 C5 C6 . . 109.67(9) ?
N1 C5 C15 . . 111.40(9) ?
C6 C5 C15 . . 112.81(9) ?
N1 C5 H5 . . 107.6 ?
C6 C5 H5 . . 107.6 ?
C15 C5 H5 . . 107.6 ?
B1 O4 C24 . . 106.94(8) ?
N1 C4 C3 . . 123.04(10) ?
N1 C4 H4 . . 118.5 ?
C3 C4 H4 . . 118.5 ?
C6 C7 C3 . . 120.43(11) ?
C6 C7 H7 . . 119.8 ?
C3 C7 H7 . . 119.8 ?
N1 C8 C9 . . 112.73(10) ?
N1 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
N1 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C14 . . 118.81(13) ?
C10 C9 C8 . . 121.32(11) ?
C14 C9 C8 . . 119.84(13) ?
C12 C13 C14 . . 120.38(15) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C24 C26 H26A . . 109.5 ?
C24 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C24 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O4 C24 C25 . . 105.97(10) ?
O4 C24 C26 . . 108.92(9) ?
C25 C24 C26 . . 110.44(10) ?
O4 C24 C21 . . 102.66(8) ?
C25 C24 C21 . . 113.72(10) ?
C26 C24 C21 . . 114.41(11) ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O3 C21 C22 . . 108.21(9) ?
O3 C21 C23 . . 106.54(9) ?
C22 C21 C23 . . 110.51(10) ?
O3 C21 C24 . . 102.47(8) ?
C22 C21 C24 . . 114.52(10) ?
C23 C21 C24 . . 113.81(10) ?
C19 C20 C17 . . 113.69(11) ?
C19 C20 H20 . . 123.2 ?
C17 C20 H20 . . 123.2 ?
C20 C19 S1 . . 111.13(9) ?
C20 C19 H19 . . 124.4 ?
S1 C19 H19 . . 124.4 ?
C17 C18 S1 . . 112.39(9) ?
C17 C18 H18 . . 123.8 ?
S1 C18 H18 . . 123.8 ?
C18 C17 C20 . . 111.01(11) ?
C18 C17 C16 . . 124.85(11) ?
C20 C17 C16 . . 124.11(10) ?
C17 C16 C15 . . 112.26(9) ?
C17 C16 H16A . . 109.2 ?
C15 C16 H16A . . 109.2 ?
C17 C16 H16B . . 109.2 ?
C15 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C16 C15 C5 . . 111.76(9) ?
C16 C15 B1 . . 111.11(9) ?
C5 C15 B1 . . 110.57(9) ?
C16 C15 H15 . . 107.7 ?
C5 C15 H15 . . 107.7 ?
B1 C15 H15 . . 107.7 ?
C9 C14 C13 . . 120.54(16) ?
C9 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C13 C12 C11 . . 119.69(14) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C11 C10 . . 120.21(16) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C9 C10 C11 . . 120.37(14) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C19 . 1.7046(14) ?
S1 C18 . 1.7151(13) ?
B1 O3 . 1.3622(14) ?
B1 O4 . 1.3672(14) ?
B1 C15 . 1.5811(15) ?
N1 C4 . 1.3407(15) ?
N1 C8 . 1.4566(15) ?
N1 C5 . 1.4836(13) ?
C1 O1 . 1.4338(16) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
O1 C2 . 1.3574(15) ?
O2 C2 . 1.2203(15) ?
C2 C3 . 1.4459(16) ?
O3 C21 . 1.4612(12) ?
C3 C4 . 1.3668(17) ?
C3 C7 . 1.4541(16) ?
C6 C7 . 1.3346(17) ?
C6 C5 . 1.5065(16) ?
C6 H6 . 0.95 ?
C5 C15 . 1.5540(15) ?
C5 H5 . 1.0 ?
O4 C24 . 1.4656(13) ?
C4 H4 . 0.95 ?
C7 H7 . 0.95 ?
C8 C9 . 1.5150(18) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.387(2) ?
C9 C14 . 1.3891(18) ?
C13 C12 . 1.372(3) ?
C13 C14 . 1.391(2) ?
C13 H13 . 0.95 ?
C26 C24 . 1.5207(17) ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C25 C24 . 1.5196(18) ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C24 C21 . 1.5610(15) ?
C23 C21 . 1.5223(17) ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C22 C21 . 1.5150(16) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C20 C19 . 1.3563(19) ?
C20 C17 . 1.4245(16) ?
C20 H20 . 0.95 ?
C19 H19 . 0.95 ?
C18 C17 . 1.3553(17) ?
C18 H18 . 0.95 ?
C17 C16 . 1.5021(16) ?
C16 C15 . 1.5420(15) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C15 H15 . 1.0 ?
C14 H14 . 0.95 ?
C12 C11 . 1.384(2) ?
C12 H12 . 0.95 ?
C11 C10 . 1.393(2) ?
C11 H11 . 0.95 ?
C10 H10 . 0.95 ?
