#------------------------------------------------------------------------------
#$Date: 2021-08-30 09:29:47 +0300 (Mon, 30 Aug 2021) $
#$Revision: 268283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/33/4103363.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_4103363
loop_
_publ_author_name
'Andrey Solovyev'
'Qianli Chu'
'Steven J. Geib'
'Louis Fensterbank'
'Max Malacria'
'Emmanuel Lacôte'
'Dennis P. Curran'
_publ_section_title
;
 Substitution Reactions at Tetracoordinate Boron: Synthesis of
 N-Heterocyclic Carbene Boranes with Boron-Heteroatom Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15072
_journal_page_last               15080
_journal_paper_doi               10.1021/ja107025y
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C27 H35 I N2'
_chemical_formula_weight         514.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7146(13)
_cell_length_b                   12.8217(16)
_cell_length_c                   19.089(2)
_cell_measurement_reflns_used    5935
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.17
_cell_measurement_theta_min      2.48
_cell_volume                     2622.4(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30853
_diffrn_reflns_theta_full        32.35
_diffrn_reflns_theta_max         32.35
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_T_max  0.7475
_exptl_absorpt_correction_T_min  0.5770
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       robm
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                3913
_reflns_number_total             4531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja107025y_si_010.cif
_cod_data_source_block           chu628s
_cod_depositor_comments
;

2021-08-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C108 H140 I4 N8'
_cod_original_formula_weight         2057.88
_cod_original_formula_units_Z            1
_cod_database_code               4103363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I I 0.2500 0.2500 0.313883(7) 0.03797(8) Uani 1 2 d S
N N 0.28077(10) 0.16941(7) 0.07898(6) 0.02204(18) Uani 1 1 d .
C1 C 0.2500 0.2500 0.12049(11) 0.0207(3) Uani 1 2 d S
H1 H 0.2500 0.2500 0.172(2) 0.030(9) Uiso 1 2 d S
C2 C 0.26921(12) 0.19976(10) 0.00956(7) 0.0256(2) Uani 1 1 d .
H2 H 0.2870(16) 0.1575(13) -0.0273(9) 0.030(4) Uiso 1 1 d .
C3 C 0.32291(11) 0.06896(8) 0.10439(6) 0.0230(2) Uani 1 1 d .
C4 C 0.45145(12) 0.05466(9) 0.11337(7) 0.0273(2) Uani 1 1 d .
C5 C 0.49027(13) -0.04228(10) 0.13828(8) 0.0344(3) Uani 1 1 d .
H5 H 0.5796(15) -0.0584(13) 0.1446(9) 0.033(4) Uiso 1 1 d .
C6 C 0.40421(14) -0.11932(10) 0.15380(9) 0.0383(3) Uani 1 1 d .
H6 H 0.4315(19) -0.1883(17) 0.1728(10) 0.050(5) Uiso 1 1 d .
C7 C 0.27773(15) -0.10264(11) 0.14419(9) 0.0353(3) Uani 1 1 d .
H7 H 0.215(2) -0.1582(17) 0.1592(12) 0.046(5) Uiso 1 1 d .
C8 C 0.23342(12) -0.00740(10) 0.11818(8) 0.0266(2) Uani 1 1 d .
C9 C 0.54546(12) 0.14122(10) 0.10078(8) 0.0332(3) Uani 1 1 d .
H9 H 0.5074(16) 0.1976(16) 0.0740(10) 0.042(5) Uiso 1 1 d .
C10 C 0.65851(19) 0.10349(18) 0.05910(11) 0.0545(5) Uani 1 1 d .
H10A H 0.716(3) 0.165(2) 0.0491(13) 0.061(7) Uiso 1 1 d .
H10B H 0.631(2) 0.0737(17) 0.0144(12) 0.058(6) Uiso 1 1 d .
H10C H 0.703(4) 0.045(3) 0.0881(17) 0.107(9) Uiso 1 1 d .
C11 C 0.58632(18) 0.18784(16) 0.17077(11) 0.0539(5) Uani 1 1 d .
H11B H 0.627(3) 0.2454(16) 0.156(2) 0.062(8) Uiso 1 1 d .
H11C H 0.520(3) 0.207(3) 0.1954(13) 0.071(7) Uiso 1 1 d .
C12 C 0.09454(12) 0.01007(10) 0.10819(8) 0.0317(3) Uani 1 1 d .
H12 H 0.0861(17) 0.0729(14) 0.0777(10) 0.041(5) Uiso 1 1 d .
C13 C 0.03151(18) 0.03147(19) 0.17855(10) 0.0506(4) Uani 1 1 d .
H13A H -0.0584(19) 0.0462(16) 0.1719(10) 0.044(5) Uiso 1 1 d .
H13B H 0.069(2) 0.089(2) 0.2019(14) 0.070(7) Uiso 1 1 d .
H13C H 0.034(2) -0.032(2) 0.2087(13) 0.071(7) Uiso 1 1 d .
C14 C 0.03195(17) -0.08140(14) 0.07063(10) 0.0448(4) Uani 1 1 d .
H14A H -0.0536(19) -0.0632(14) 0.0617(9) 0.044(5) Uiso 1 1 d .
H14B H 0.022(2) -0.1438(17) 0.1035(12) 0.059(6) Uiso 1 1 d .
H14C H 0.072(2) -0.0954(18) 0.0236(15) 0.070(7) Uiso 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'
I I -0.4742 1.8119 '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
C1 N C2 109.02(12) . .
C1 N C3 124.26(11) . .
C2 N C3 126.69(10) . .
N C1 N 107.70(17) . 2
N C1 H1 126.15(8) . .
N C1 H1 126.15(8) 2 .
C2 C2 N 107.13(7) 2 .
C2 C2 H2 129.2(11) 2 .
N C2 H2 123.6(11) . .
C8 C3 C4 124.12(11) . .
C8 C3 N 118.22(11) . .
C4 C3 N 117.66(10) . .
C5 C4 C3 116.88(12) . .
C5 C4 C9 120.52(12) . .
C3 C4 C9 122.52(11) . .
C6 C5 C4 120.71(12) . .
C6 C5 H5 118.1(9) . .
C4 C5 H5 121.2(10) . .
C5 C6 C7 120.92(12) . .
C5 C6 H6 121.0(12) . .
C7 C6 H6 118.1(12) . .
C6 C7 C8 120.89(13) . .
C6 C7 H7 119.9(13) . .
C8 C7 H7 119.0(13) . .
C3 C8 C7 116.46(12) . .
C3 C8 C12 123.14(11) . .
C7 C8 C12 120.37(12) . .
C4 C9 C11 109.74(13) . .
C4 C9 C10 112.15(13) . .
C11 C9 C10 110.62(14) . .
C4 C9 H9 110.4(11) . .
C11 C9 H9 106.7(11) . .
C10 C9 H9 107.1(11) . .
C9 C10 H10A 109.4(14) . .
C9 C10 H10B 109.8(13) . .
H10A C10 H10B 108.7(19) . .
C9 C10 H10C 108(2) . .
H10A C10 H10C 112(3) . .
H10B C10 H10C 108(2) . .
C9 C11 H11B 101(2) . .
C9 C11 H11C 110.2(18) . .
H11B C11 H11C 109(3) . .
C8 C12 C13 110.46(13) . .
C8 C12 C14 112.08(13) . .
C13 C12 C14 110.85(14) . .
C8 C12 H12 106.3(10) . .
C13 C12 H12 109.1(11) . .
C14 C12 H12 107.8(11) . .
C12 C13 H13A 110.5(11) . .
C12 C13 H13B 111.4(15) . .
H13A C13 H13B 109.0(19) . .
C12 C13 H13C 110.4(15) . .
H13A C13 H13C 104.7(19) . .
H13B C13 H13C 111(2) . .
C12 C14 H14A 108.3(11) . .
C12 C14 H14B 110.9(13) . .
H14A C14 H14B 101.8(16) . .
C12 C14 H14C 111.5(14) . .
H14A C14 H14C 106.8(18) . .
H14B C14 H14C 116.7(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C1 1.3433(15) .
N C2 1.3866(17) .
N C3 1.4484(14) .
C1 N 1.3433(15) 2
C1 H1 0.97(4) .
C2 C2 1.352(3) 2
C2 H2 0.908(18) .
C3 C8 1.3954(17) .
C3 C4 1.4000(17) .
C4 C5 1.3942(17) .
C4 C9 1.5180(18) .
C5 C6 1.383(2) .
C5 H5 0.987(16) .
C6 C7 1.384(2) .
C6 H6 1.00(2) .
C7 C8 1.4010(18) .
C7 H7 1.02(2) .
C8 C12 1.5169(18) .
C9 C11 1.528(2) .
C9 C10 1.528(2) .
C9 H9 0.97(2) .
C10 H10A 1.02(3) .
C10 H10B 0.98(2) .
C10 H10C 1.05(3) .
C11 H11B 0.90(3) .
C11 H11C 0.88(3) .
C12 C13 1.528(2) .
C12 C14 1.529(2) .
C12 H12 0.999(18) .
C13 H13A 0.99(2) .
C13 H13B 0.95(3) .
C13 H13C 1.00(3) .
C14 H14A 0.96(2) .
C14 H14B 1.02(2) .
C14 H14C 1.01(3) .
