#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:27:25 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038079.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_4038079
loop_
_publ_author_name
'Sarkar, Nabin'
'Bera, Subhadeep'
'Nembenna, Sharanappa'
_publ_section_title
;
 Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A
 Multifunctional Catalyst.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4999
_journal_page_last               5009
_journal_paper_doi               10.1021/acs.joc.0c00234
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C20 H33 B2 N O4'
_chemical_formula_sum            'C20 H33 B2 N O4'
_chemical_formula_weight         373.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.779(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0036(3)
_cell_length_b                   24.1961(6)
_cell_length_c                   15.6222(4)
_cell_measurement_reflns_used    12736
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      77.0070
_cell_measurement_theta_min      4.2870
_cell_volume                     4320.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -102.00 -52.00   0.50    0.50    --  -38.50-157.00  22.00  100
  2  ω   -107.00 -19.00   0.50    0.50    --  -38.50 157.00  57.00  176
  3  ω    -85.00   4.00   0.50    0.50    --  -38.50 118.00 -97.00  178
  4  ω     18.00  96.00   0.50    0.50    --   49.31-118.00 176.00  156
  5  ω     41.00 118.00   0.50    0.50    --   49.31-157.00  22.00  154
  6  ω     43.00 139.00   0.50    1.96    --  106.38-157.00  22.00  192
  7  ω     40.00 113.00   0.50    1.96    --  106.38-118.00 176.00  146
  8  ω     98.00 173.00   0.50    1.96    --  106.38 118.00 -97.00  150
  9  ω     73.00 166.00   0.50    1.96    --  106.38 157.00  57.00  186
 10  ω   -103.00 -15.00   0.50    0.50    --  -38.50 -77.00   0.00  176
 11  ω    -42.00  28.00   0.50    0.50    --  -38.50  37.00 -90.00  140
 12  ω     46.00 116.00   0.50    0.50    --   49.31  37.00   0.00  140
 13  ω     46.00 116.00   0.50    0.50    --   49.31  37.00 -60.00  140
 14  ω     38.00 110.00   0.50    1.96    --  106.38 -94.00-180.00  144
 15  ω     93.00 169.00   0.50    1.96    --  106.38  61.00 -30.00  152
 16  ω     44.00 120.00   0.50    1.96    --  106.38 -61.00 -30.00  152
 17  ω     93.00 169.00   0.50    1.96    --  106.38  61.00  60.00  152
 18  ω     38.00 115.00   0.50    1.96    --  106.38 -15.00   0.00  154
 19  ω     39.00 109.00   0.50    1.96    --  106.38 -94.00-150.00  140
 20  ω     45.00 109.00   0.50    1.96    --  106.38 -30.00 150.00  128
 21  ω    110.00 170.00   0.50    1.96    --  106.38  45.00   0.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0867949000
_diffrn_orient_matrix_UB_12      -0.0482013000
_diffrn_orient_matrix_UB_13      -0.0089725000
_diffrn_orient_matrix_UB_21      0.0940867000
_diffrn_orient_matrix_UB_22      -0.0408389000
_diffrn_orient_matrix_UB_23      -0.0091869000
_diffrn_orient_matrix_UB_31      0.0422420000
_diffrn_orient_matrix_UB_32      -0.0077443000
_diffrn_orient_matrix_UB_33      0.1027695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18626
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.169
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1030P)²+1.3410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3899
_reflns_number_total             4398
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00234_si_003.cif
_cod_data_source_block           sn-ns-intrtmediate
_cod_depositor_comments
'Adding full bibliography for 4038079--4038080.cif.'
_cod_original_cell_volume        4320.63(19)
_cod_database_code               4038079
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C168 H264 B16 O32 '
_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.
;
_diffrn_oxdiff_ac3_digest_frames
;
01dd14db5cff1cd385aef35c3c735f5457000460b13
;
_diffrn_oxdiff_ac3_digest_hkl
;
01bc5e080bf82043238b97fca1a45e247ec83d
;
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C14(H14A,H14B,
 H14C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 11.626
_oxdiff_exptl_absorpt_empirical_full_min 0.381
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O1 O 0.61235(8) 0.05705(4) 0.10149(6) 0.0402(3) Uani 1 1 d . . . . .
O3 O 0.94241(9) 0.05773(4) 0.37838(6) 0.0482(3) Uani 1 1 d . . . . .
N1 N 0.77710(9) 0.05869(4) 0.24011(7) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.63914(9) 0.13627(4) 0.18576(6) 0.0449(3) Uani 1 1 d . . . . .
O4 O 0.84361(10) 0.13904(4) 0.34021(7) 0.0524(3) Uani 1 1 d . . . . .
C3 C 0.74199(12) -0.09932(6) 0.25825(8) 0.0393(3) Uani 1 1 d . . . . .
C1 C 0.79887(11) -0.00044(5) 0.22628(8) 0.0368(3) Uani 1 1 d . . . . .
H1A H 0.8814 -0.0084 0.2530 0.044 Uiso 1 1 calc R . . . .
H1B H 0.7785 -0.0080 0.1624 0.044 Uiso 1 1 calc R . . . .
B2 B 0.85263(13) 0.08518(6) 0.31802(9) 0.0366(3) Uani 1 1 d . . . . .
B1 B 0.67872(12) 0.08411(6) 0.17735(9) 0.0339(3) Uani 1 1 d . . . . .
C10 C 0.54888(12) 0.14884(6) 0.10168(9) 0.0414(3) Uani 1 1 d . . . . .
C9 C 0.50753(12) 0.09016(6) 0.06417(9) 0.0436(3) Uani 1 1 d . . . . .
C12 C 0.94646(14) 0.15250(6) 0.41480(9) 0.0476(4) Uani 1 1 d . . . . .
C11 C 0.99362(12) 0.09449(6) 0.45362(8) 0.0431(3) Uani 1 1 d . . . . .
C2 C 0.72790(13) -0.03762(6) 0.26786(9) 0.0440(3) Uani 1 1 d . . . . .
H2A H 0.6459 -0.0285 0.2413 0.053 Uiso 1 1 calc R . . . .
H2B H 0.7485 -0.0290 0.3314 0.053 Uiso 1 1 calc R . . . .
C4 C 0.82282(17) -0.12238(7) 0.22264(12) 0.0579(4) Uani 1 1 d . . . . .
H4 H 0.8729 -0.0995 0.2037 0.069 Uiso 1 1 calc R . . . .
C15 C 0.45618(16) 0.18424(7) 0.12234(11) 0.0579(4) Uani 1 1 d . . . . .
H15A H 0.4259 0.1653 0.1645 0.087 Uiso 1 1 calc GR . . . .
H15B H 0.3938 0.1911 0.0679 0.087 Uiso 1 1 calc GR . . . .
H15C H 0.4901 0.2188 0.1477 0.087 Uiso 1 1 calc GR . . . .
C16 C 0.60764(16) 0.18082(7) 0.04358(12) 0.0587(4) Uani 1 1 d . . . . .
H16A H 0.6459 0.2128 0.0757 0.088 Uiso 1 1 calc GR . . . .
H16B H 0.5498 0.1922 -0.0109 0.088 Uiso 1 1 calc GR . . . .
H16C H 0.6643 0.1576 0.0292 0.088 Uiso 1 1 calc GR . . . .
C18 C 1.12540(15) 0.08757(9) 0.48039(12) 0.0653(5) Uani 1 1 d . . . . .
H18A H 1.1460 0.0508 0.5027 0.098 Uiso 1 1 calc GR . . . .
H18B H 1.1620 0.1138 0.5265 0.098 Uiso 1 1 calc GR . . . .
H18C H 1.1516 0.0937 0.4290 0.098 Uiso 1 1 calc GR . . . .
C6 C 0.7607(2) -0.21414(8) 0.24335(14) 0.0778(6) Uani 1 1 d . . . . .
H6 H 0.7669 -0.2522 0.2384 0.093 Uiso 1 1 calc R . . . .
C14 C 0.4703(2) 0.08524(8) -0.03712(11) 0.0734(6) Uani 1 1 d . . . . .
H14A H 0.5351 0.0942 -0.0584 0.110 Uiso 1 1 calc GR . . . .
H14B H 0.4069 0.1103 -0.0630 0.110 Uiso 1 1 calc GR . . . .
H14C H 0.4453 0.0481 -0.0543 0.110 Uiso 1 1 calc GR . . . .
C8 C 0.67097(18) -0.13495(7) 0.28647(13) 0.0642(5) Uani 1 1 d . . . . .
H8 H 0.6151 -0.1207 0.3106 0.077 Uiso 1 1 calc R . . . .
C5 C 0.8310(2) -0.17950(8) 0.21450(15) 0.0744(6) Uani 1 1 d . . . . .
H5 H 0.8853 -0.1941 0.1890 0.089 Uiso 1 1 calc R . . . .
C13 C 0.41423(16) 0.06640(8) 0.10069(16) 0.0718(5) Uani 1 1 d . . . . .
H13A H 0.4018 0.0282 0.0839 0.108 Uiso 1 1 calc GR . . . .
H13B H 0.3426 0.0865 0.0762 0.108 Uiso 1 1 calc GR . . . .
H13C H 0.4393 0.0695 0.1650 0.108 Uiso 1 1 calc GR . . . .
C7 C 0.6814(2) -0.19201(9) 0.27953(17) 0.0852(7) Uani 1 1 d . . . . .
H7 H 0.6333 -0.2153 0.3000 0.102 Uiso 1 1 calc R . . . .
C20 C 1.0297(2) 0.18377(9) 0.37610(14) 0.0757(6) Uani 1 1 d . . . . .
H20A H 1.0549 0.1600 0.3364 0.114 Uiso 1 1 calc GR . . . .
H20B H 1.0965 0.1958 0.4241 0.114 Uiso 1 1 calc GR . . . .
H20C H 0.9904 0.2154 0.3433 0.114 Uiso 1 1 calc GR . . . .
C17 C 0.94988(18) 0.07585(8) 0.53045(11) 0.0637(5) Uani 1 1 d . . . . .
H17A H 0.8663 0.0794 0.5131 0.096 Uiso 1 1 calc GR . . . .
H17B H 0.9845 0.0984 0.5823 0.096 Uiso 1 1 calc GR . . . .
H17C H 0.9712 0.0379 0.5445 0.096 Uiso 1 1 calc GR . . . .
C19 C 0.9076(2) 0.18929(8) 0.47829(13) 0.0744(6) Uani 1 1 d . . . . .
H19A H 0.8801 0.2238 0.4492 0.112 Uiso 1 1 calc GR . . . .
H19B H 0.9724 0.1959 0.5312 0.112 Uiso 1 1 calc GR . . . .
H19C H 0.8456 0.1716 0.4948 0.112 Uiso 1 1 calc GR . . . .
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'
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
B1 O1 C9 106.60(10) . . ?
B2 O3 C11 108.08(10) . . ?
B2 N1 C1 117.59(10) . . ?
B1 N1 C1 117.57(10) . . ?
B1 N1 B2 124.75(11) . . ?
B1 O2 C10 106.88(9) . . ?
B2 O4 C12 107.75(10) . . ?
C4 C3 C2 123.63(13) . . ?
C4 C3 C8 117.26(15) . . ?
C8 C3 C2 119.12(14) . . ?
N1 C1 C2 111.32(11) . . ?
O3 B2 N1 122.07(12) . . ?
O4 B2 O3 113.36(11) . . ?
O4 B2 N1 124.58(12) . . ?
O1 B1 N1 121.88(11) . . ?
O2 B1 O1 113.26(11) . . ?
O2 B1 N1 124.85(11) . . ?
O2 C10 C9 102.27(10) . . ?
O2 C10 C15 108.56(11) . . ?
O2 C10 C16 106.96(12) . . ?
C15 C10 C9 115.15(13) . . ?
C15 C10 C16 110.14(12) . . ?
C16 C10 C9 113.07(13) . . ?
O1 C9 C10 102.35(10) . . ?
O1 C9 C14 108.61(13) . . ?
O1 C9 C13 106.75(12) . . ?
C14 C9 C10 115.06(13) . . ?
C14 C9 C13 110.35(15) . . ?
C13 C9 C10 113.01(14) . . ?
O4 C12 C11 103.18(10) . . ?
O4 C12 C20 107.10(13) . . ?
O4 C12 C19 107.59(14) . . ?
C20 C12 C11 113.39(15) . . ?
C19 C12 C11 114.97(13) . . ?
C19 C12 C20 109.93(15) . . ?
O3 C11 C12 102.82(9) . . ?
O3 C11 C18 107.67(13) . . ?
O3 C11 C17 107.15(12) . . ?
C18 C11 C12 115.41(13) . . ?
C18 C11 C17 109.43(14) . . ?
C17 C11 C12 113.67(14) . . ?
C1 C2 C3 116.63(11) . . ?
C3 C4 C5 121.15(18) . . ?
C7 C6 C5 118.68(18) . . ?
C3 C8 C7 121.08(19) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C7 C8 121.0(2) . . ?
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
O1 B1 1.3753(15) . ?
O1 C9 1.4549(16) . ?
O3 B2 1.3679(16) . ?
O3 C11 1.4523(15) . ?
N1 C1 1.4818(16) . ?
N1 B2 1.4285(16) . ?
N1 B1 1.4238(16) . ?
O2 B1 1.3688(16) . ?
O2 C10 1.4569(14) . ?
O4 B2 1.3612(17) . ?
O4 C12 1.4524(15) . ?
C3 C2 1.5150(19) . ?
C3 C4 1.375(2) . ?
C3 C8 1.376(2) . ?
C1 C2 1.515(2) . ?
C10 C9 1.558(2) . ?
C10 C15 1.515(2) . ?
C10 C16 1.520(2) . ?
C9 C14 1.512(2) . ?
C9 C13 1.517(2) . ?
C12 C11 1.565(2) . ?
C12 C20 1.519(2) . ?
C12 C19 1.509(2) . ?
C11 C18 1.517(2) . ?
C11 C17 1.518(2) . ?
C4 C5 1.394(2) . ?
C6 C5 1.360(3) . ?
C6 C7 1.357(4) . ?
C8 C7 1.394(3) . ?
