#------------------------------------------------------------------------------
#$Date: 2020-12-19 00:15:20 +0200 (Sat, 19 Dec 2020) $
#$Revision: 259953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/83/4518327.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_4518327
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            'C28 H33 B Br N O4'
_chemical_formula_weight         538.28
_chemical_name_common            Rajender052820_1
_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     direct
_cell_angle_alpha                74.6461(9)
_cell_angle_beta                 84.2332(9)
_cell_angle_gamma                88.2173(9)
_cell_formula_units_Z            2
_cell_length_a                   10.0807(4)
_cell_length_b                   11.1859(5)
_cell_length_c                   12.2258(5)
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    110.(2)
_cell_measurement_theta_max      70.1801
_cell_measurement_theta_min      3.7666
_cell_volume                     1322.66(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      110.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            129089
_diffrn_reflns_theta_full        70.09
_diffrn_reflns_theta_max         74.93
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    2.384
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.23
_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    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.833
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0351
_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)+(0.0341P)²+1.4764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                5342
_reflns_number_total             5345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c04474_si_003.cif
_cod_data_source_block           Rajender052820_1
_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_original_cell_volume        1322.66(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4518327
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
Br Br1 -0.13244(2) 0.65629(2) 1.00290(2) 0.03095(9) Uani d . . . 1 . .
B B1 0.39114(19) 0.47818(16) 0.74887(15) 0.0133(3) Uani d . . . 1 . .
C C1 0.3522(2) 1.10111(19) 0.22763(16) 0.0292(4) Uani d . . . 1 . .
H H1 0.299532 1.065921 0.180649 0.044 Uiso calc U . R 1 . .
H H00Q 0.441797 1.120858 0.188865 0.044 Uiso calc U . R 1 . .
H H00R 0.308758 1.176852 0.239562 0.044 Uiso calc U . R 1 . .
N N1 0.16592(13) 0.77193(13) 0.68635(12) 0.0134(3) Uani d . . . 1 . .
O O1 0.36163(13) 1.01288(12) 0.33560(10) 0.0203(3) Uani d . . . 1 . .
O O2 0.13755(13) 1.01751(12) 0.36546(11) 0.0206(3) Uani d . . . 1 . .
C C2 0.24424(17) 0.97763(15) 0.39926(14) 0.0145(3) Uani d . . . 1 . .
O O4 0.42680(13) 0.46675(12) 0.85610(10) 0.0206(3) Uani d . . . 1 . .
C C4 0.15703(16) 0.85508(14) 0.58600(14) 0.0130(3) Uani d . . . 1 . .
H H4 0.072566 0.891194 0.568704 0.016 Uiso calc U . R 1 . .
O O3 0.46998(12) 0.41076(11) 0.68945(10) 0.0180(3) Uani d . . . 1 . .
C C3 0.26481(16) 0.89032(14) 0.50709(14) 0.0135(3) Uani d . . . 1 . .
C C9 0.08222(17) 0.80897(15) 0.87213(14) 0.0161(3) Uani d . . . 1 . .
C C7 0.28670(16) 0.69457(15) 0.71283(14) 0.0129(3) Uani d . . . 1 . .
H H7 0.301435 0.688153 0.793866 0.015 Uiso calc U . R 1 . .
C C5 0.39538(16) 0.84518(15) 0.54120(15) 0.0153(3) Uani d . . . 1 . .
H H5 0.473477 0.877697 0.493793 0.018 Uiso calc U . R 1 . .
C C6 0.40608(16) 0.75814(15) 0.63895(15) 0.0153(3) Uani d . . . 1 . .
H H6 0.492385 0.735617 0.662615 0.018 Uiso calc U . R 1 . .
C C8 0.05568(16) 0.75353(16) 0.77541(14) 0.0155(3) Uani d . . . 1 . .
H H00A 0.039194 0.663578 0.806523 0.019 Uiso calc U . R 1 . .
H H8 -0.025817 0.791909 0.741862 0.019 Uiso calc U . R 1 . .
C C25 0.5524(3) 0.3150(3) 0.98561(17) 0.0467(7) Uani d . . . 1 . .
H H0AA 0.55593 0.367381 1.038066 0.07 Uiso calc U . R 1 . .
H HB 0.630391 0.260011 0.990946 0.07 Uiso calc U . R 1 . .
H HC 0.470944 0.265193 1.005956 0.07 Uiso calc U . R 1 . .
C C28 0.4666(2) 0.20603(19) 0.8132(2) 0.0359(5) Uani d . . . 1 . .
H H28 0.38055 0.222512 0.851589 0.054 Uiso calc U . R 1 . .
H H00X 0.516061 0.144037 0.866675 0.054 Uiso calc U . R 1 . .
H H00Y 0.451674 0.174682 0.74785 0.054 Uiso calc U . R 1 . .
C C27 0.68106(19) 0.30132(18) 0.71453(15) 0.0236(4) Uani d . . . 1 . .
H H00J 0.66882 0.255325 0.658323 0.035 Uiso calc U . R 1 . .
H H00M 0.736843 0.25262 0.771736 0.035 Uiso calc U . R 1 . .
H H27 0.72456 0.380539 0.676179 0.035 Uiso calc U . R 1 . .
C C26 0.54656(18) 0.32526(16) 0.77227(15) 0.0191(4) Uani d . . . 1 . .
C C24 0.6654(2) 0.4890(2) 0.8391(2) 0.0401(6) Uani d . . . 1 . .
H H00 0.667377 0.537738 0.759488 0.06 Uiso calc U . R 1 . .
H H 0.750312 0.444817 0.851507 0.06 Uiso calc U . R 1 . .
H HA 0.651345 0.54442 0.889314 0.06 Uiso calc U . R 1 . .
C C23 0.5521(2) 0.39577(19) 0.86536(15) 0.0238(4) Uani d . . . 1 . .
C C22 0.28458(18) 0.35946(18) 0.51967(17) 0.0228(4) Uani d . . . 1 . .
H H22 0.370823 0.38874 0.486782 0.027 Uiso calc U . R 1 . .
C C21 0.24381(19) 0.24384(19) 0.51474(19) 0.0273(4) Uani d . . . 1 . .
H H00S 0.302058 0.194908 0.478055 0.033 Uiso calc U . R 1 . .
C C20 0.11859(19) 0.19916(17) 0.56301(17) 0.0223(4) Uani d . . . 1 . .
H H20 0.091916 0.118921 0.561594 0.027 Uiso calc U . R 1 . .
C C19 0.03287(18) 0.27273(18) 0.61329(16) 0.0212(4) Uani d . . . 1 . .
H H19 -0.053838 0.243762 0.645024 0.025 Uiso calc U . R 1 . .
C C18 0.07368(17) 0.38902(17) 0.61734(15) 0.0191(3) Uani d . . . 1 . .
H H18 0.013957 0.439128 0.651424 0.023 Uiso calc U . R 1 . .
C C17 0.20036(17) 0.43307(15) 0.57233(14) 0.0149(3) Uani d . . . 1 . .
C C16 0.24515(18) 0.55840(15) 0.57955(14) 0.0162(3) Uani d . . . 1 . .
H H00H 0.17644 0.6211 0.551394 0.019 Uiso calc U . R 1 . .
H H16 0.328564 0.581663 0.529059 0.019 Uiso calc U . R 1 . .
C C15 0.26935(16) 0.56089(14) 0.70147(13) 0.0128(3) Uani d . . . 1 . .
H H15 0.187937 0.525852 0.752124 0.015 Uiso calc U . R 1 . .
C C14 0.00907(18) 0.77177(17) 0.97870(15) 0.0206(4) Uani d . . . 1 . .
C C13 0.0315(2) 0.81989(19) 1.06902(16) 0.0273(4) Uani d . . . 1 . .
H H00U -0.019161 0.791716 1.14075 0.033 Uiso calc U . R 1 . .
C C12 0.1281(2) 0.90905(19) 1.05321(18) 0.0300(5) Uani d . . . 1 . .
H H00Z 0.144677 0.942569 1.114269 0.036 Uiso calc U . R 1 . .
C C11 0.2011(2) 0.94961(18) 0.94818(19) 0.0280(4) Uani d . . . 1 . .
H H11 0.266921 1.011734 0.936933 0.034 Uiso calc U . R 1 . .
C C10 0.17802(19) 0.89950(16) 0.85899(17) 0.0213(4) Uani d . . . 1 . .
H H00T 0.229048 0.92792 0.787484 0.026 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'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 B1 O4 . . 113.37(15) ?
O3 B1 C15 . . 124.50(15) ?
O4 B1 C15 . . 122.13(15) ?
O1 C1 H1 . . 109.5 ?
O1 C1 H00Q . . 109.5 ?
H1 C1 H00Q . . 109.5 ?
O1 C1 H00R . . 109.5 ?
H1 C1 H00R . . 109.5 ?
H00Q C1 H00R . . 109.5 ?
C4 N1 C8 . . 120.81(13) ?
C4 N1 C7 . . 122.47(14) ?
C8 N1 C7 . . 116.72(13) ?
C2 O1 C1 . . 115.84(14) ?
O2 C2 O1 . . 121.77(15) ?
O2 C2 C3 . . 126.74(16) ?
O1 C2 C3 . . 111.49(14) ?
B1 O4 C23 . . 106.84(13) ?
N1 C4 C3 . . 122.73(15) ?
N1 C4 H4 . . 118.6 ?
C3 C4 H4 . . 118.6 ?
B1 O3 C26 . . 106.42(13) ?
C4 C3 C2 . . 118.62(15) ?
C4 C3 C5 . . 117.38(15) ?
C2 C3 C5 . . 123.79(15) ?
C10 C9 C14 . . 116.75(17) ?
C10 C9 C8 . . 122.15(16) ?
C14 C9 C8 . . 121.09(16) ?
N1 C7 C6 . . 109.58(13) ?
N1 C7 C15 . . 112.03(13) ?
C6 C7 C15 . . 112.05(13) ?
N1 C7 H7 . . 107.7 ?
C6 C7 H7 . . 107.7 ?
C15 C7 H7 . . 107.7 ?
C6 C5 C3 . . 120.40(16) ?
C6 C5 H5 . . 119.8 ?
C3 C5 H5 . . 119.8 ?
C5 C6 C7 . . 122.55(15) ?
C5 C6 H6 . . 118.7 ?
C7 C6 H6 . . 118.7 ?
N1 C8 C9 . . 112.60(14) ?
N1 C8 H00A . . 109.1 ?
C9 C8 H00A . . 109.1 ?
N1 C8 H8 . . 109.1 ?
C9 C8 H8 . . 109.1 ?
H00A C8 H8 . . 107.8 ?
C23 C25 H0AA . . 109.5 ?
C23 C25 HB . . 109.5 ?
H0AA C25 HB . . 109.5 ?
C23 C25 HC . . 109.5 ?
H0AA C25 HC . . 109.5 ?
HB C25 HC . . 109.5 ?
C26 C28 H28 . . 109.5 ?
C26 C28 H00X . . 109.5 ?
H28 C28 H00X . . 109.5 ?
C26 C28 H00Y . . 109.5 ?
H28 C28 H00Y . . 109.5 ?
H00X C28 H00Y . . 109.5 ?
C26 C27 H00J . . 109.5 ?
C26 C27 H00M . . 109.5 ?
H00J C27 H00M . . 109.5 ?
C26 C27 H27 . . 109.5 ?
H00J C27 H27 . . 109.5 ?
H00M C27 H27 . . 109.5 ?
O3 C26 C27 . . 109.30(14) ?
O3 C26 C28 . . 106.35(16) ?
C27 C26 C28 . . 110.32(16) ?
O3 C26 C23 . . 102.11(13) ?
C27 C26 C23 . . 114.69(16) ?
C28 C26 C23 . . 113.37(17) ?
C23 C24 H00 . . 109.5 ?
C23 C24 H . . 109.5 ?
H00 C24 H . . 109.5 ?
C23 C24 HA . . 109.5 ?
H00 C24 HA . . 109.5 ?
H C24 HA . . 109.5 ?
O4 C23 C25 . . 108.47(16) ?
O4 C23 C24 . . 107.20(16) ?
C25 C23 C24 . . 110.2(2) ?
O4 C23 C26 . . 101.82(13) ?
C25 C23 C26 . . 115.34(18) ?
C24 C23 C26 . . 113.09(17) ?
C21 C22 C17 . . 120.69(17) ?
C21 C22 H22 . . 119.7 ?
C17 C22 H22 . . 119.7 ?
C20 C21 C22 . . 120.48(17) ?
C20 C21 H00S . . 119.8 ?
C22 C21 H00S . . 119.8 ?
C19 C20 C21 . . 119.32(17) ?
C19 C20 H20 . . 120.3 ?
C21 C20 H20 . . 120.3 ?
C20 C19 C18 . . 120.04(17) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C17 C18 C19 . . 121.08(16) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C18 C17 C22 . . 118.35(16) ?
C18 C17 C16 . . 120.75(15) ?
C22 C17 C16 . . 120.89(16) ?
C17 C16 C15 . . 113.09(13) ?
C17 C16 H00H . . 109.0 ?
C15 C16 H00H . . 109.0 ?
C17 C16 H16 . . 109.0 ?
C15 C16 H16 . . 109.0 ?
H00H C16 H16 . . 107.8 ?
C16 C15 C7 . . 112.65(13) ?
C16 C15 B1 . . 113.48(14) ?
C7 C15 B1 . . 109.38(13) ?
C16 C15 H15 . . 107.0 ?
C7 C15 H15 . . 107.0 ?
B1 C15 H15 . . 107.0 ?
C13 C14 C9 . . 122.52(19) ?
C13 C14 Br1 . . 117.25(15) ?
C9 C14 Br1 . . 120.18(14) ?
C12 C13 C14 . . 119.18(19) ?
C12 C13 H00U . . 120.4 ?
C14 C13 H00U . . 120.4 ?
C13 C12 C11 . . 119.88(18) ?
C13 C12 H00Z . . 120.1 ?
C11 C12 H00Z . . 120.1 ?
C12 C11 C10 . . 120.12(19) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C9 C10 C11 . . 121.54(18) ?
C9 C10 H00T . . 119.2 ?
C11 C10 H00T . . 119.2 ?
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
Br1 C14 . 1.902(2) ?
B1 O3 . 1.366(2) ?
B1 O4 . 1.366(2) ?
B1 C15 . 1.577(2) ?
C1 O1 . 1.434(2) ?
C1 H1 . 0.98 ?
C1 H00Q . 0.98 ?
C1 H00R . 0.98 ?
N1 C4 . 1.338(2) ?
N1 C8 . 1.454(2) ?
N1 C7 . 1.4837(19) ?
O1 C2 . 1.358(2) ?
O2 C2 . 1.220(2) ?
C2 C3 . 1.448(2) ?
O4 C23 . 1.469(2) ?
C4 C3 . 1.371(2) ?
C4 H4 . 0.95 ?
O3 C26 . 1.461(2) ?
C3 C5 . 1.456(2) ?
C9 C10 . 1.388(3) ?
C9 C14 . 1.398(2) ?
C9 C8 . 1.522(2) ?
C7 C6 . 1.505(2) ?
C7 C15 . 1.555(2) ?
C7 H7 . 1.0 ?
C5 C6 . 1.338(2) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C8 H00A . 0.99 ?
C8 H8 . 0.99 ?
C25 C23 . 1.508(3) ?
C25 H0AA . 0.98 ?
C25 HB . 0.98 ?
C25 HC . 0.98 ?
C28 C26 . 1.520(3) ?
C28 H28 . 0.98 ?
C28 H00X . 0.98 ?
C28 H00Y . 0.98 ?
C27 C26 . 1.514(2) ?
C27 H00J . 0.98 ?
C27 H00M . 0.98 ?
C27 H27 . 0.98 ?
C26 C23 . 1.553(2) ?
C24 C23 . 1.522(3) ?
C24 H00 . 0.98 ?
C24 H . 0.98 ?
C24 HA . 0.98 ?
C22 C21 . 1.387(3) ?
C22 C17 . 1.393(2) ?
C22 H22 . 0.95 ?
C21 C20 . 1.387(3) ?
C21 H00S . 0.95 ?
C20 C19 . 1.385(3) ?
C20 H20 . 0.95 ?
C19 C18 . 1.391(3) ?
C19 H19 . 0.95 ?
C18 C17 . 1.390(2) ?
C18 H18 . 0.95 ?
C17 C16 . 1.513(2) ?
C16 C15 . 1.542(2) ?
C16 H00H . 0.99 ?
C16 H16 . 0.99 ?
C15 H15 . 1.0 ?
C14 C13 . 1.390(3) ?
C13 C12 . 1.379(3) ?
C13 H00U . 0.95 ?
C12 C11 . 1.385(3) ?
C12 H00Z . 0.95 ?
C11 C10 . 1.393(3) ?
C11 H11 . 0.95 ?
C10 H00T . 0.95 ?
