#------------------------------------------------------------------------------
#$Date: 2017-10-13 01:32:00 +0200 (vie 13 de oct de 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/50/1505010.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_1505010
loop_
_publ_author_name
'Soutullo, Morgan D.'
'Odom, Carl I.'
'Salter, E. Alan'
'Stenson, Alexandra C.'
'Sykora, Richard E.'
'Wierzbicki, Andrzej'
'Davis, James H.'
_publ_section_title
;
 Ultra-Easy Access to NH2-Functionalized TSILs, Their Potential as Highly
 Volume-Efficient Electrophile Scavengers, and Insights into the
 Electronics of Girard's Reagent T, A Venerable Chemical Work Horse
;
_journal_issue                   4
_journal_name_full               'Journal of Combinatorial Chemistry'
_journal_page_first              571
_journal_paper_doi               10.1021/cc060151j
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C24 H20 B, C7 H16 N3 O2, C2 H3 N'
_chemical_formula_sum            'C33 H39 B N4 O2'
_chemical_formula_weight         534.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 103.870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1478(11)
_cell_length_b                   10.2584(8)
_cell_length_c                   21.693(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      12.27
_cell_measurement_theta_min      8.63
_cell_volume                     3056.6(11)
_computing_cell_refinement       'CAD4/PC v1.2'
_computing_data_collection       'CAD4/PC v1.2'
_computing_data_reduction        XCAD4PC
_computing_molecular_graphics    'SHELXP-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXCIF-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       'Th/2Th 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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5590
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.21
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9217
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          1.64
_exptl_crystal_size_mid          0.640
_exptl_crystal_size_min          0.600
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_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     363
_refine_ls_number_reflns         5359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1039P)²+0.9483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1893
_reflns_number_gt                3702
_reflns_number_total             5359
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cc060151jsi20070424_044351.cif
_cod_data_source_block           Girard4
_cod_original_cell_volume        3056.6(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1505010
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.26204(13) 0.71078(18) 1.00224(8) 0.0445(5) Uani 1 1 d .
N2 N 1.00807(14) 0.7421(2) 0.97335(11) 0.0577(6) Uani 1 1 d .
H2D H 1.0060 0.6632 0.9597 0.069 Uiso 1 1 calc R
N3 N 0.92413(14) 0.8145(2) 0.95988(10) 0.0543(5) Uani 1 1 d .
H3D H 0.9250 0.8980 0.9638 0.065 Uiso 1 1 calc R
N4 N 0.4894(5) 0.6651(6) 0.9034(2) 0.180(2) Uani 1 1 d .
O1 O 1.10373(12) 0.90163(17) 1.02443(9) 0.0620(5) Uani 1 1 d .
O2 O 0.84070(14) 0.63005(19) 0.93787(11) 0.0745(6) Uani 1 1 d .
B1 B 0.49183(17) 0.2127(3) 0.75590(11) 0.0417(6) Uani 1 1 d .
C1 C 1.2369(3) 0.7327(4) 0.93290(13) 0.0953(12) Uani 1 1 d .
H1A H 1.2951 0.7500 0.9190 0.143 Uiso 1 1 calc R
H1B H 1.1936 0.8059 0.9229 0.143 Uiso 1 1 calc R
H1C H 1.2055 0.6564 0.9118 0.143 Uiso 1 1 calc R
C2 C 1.3143(2) 0.8231(3) 1.0376(2) 0.0919(11) Uani 1 1 d .
H2A H 1.3728 0.8393 1.0238 0.138 Uiso 1 1 calc R
H2B H 1.3307 0.8039 1.0822 0.138 Uiso 1 1 calc R
H2C H 1.2734 0.8988 1.0298 0.138 Uiso 1 1 calc R
C3 C 1.3254(2) 0.5927(3) 1.01798(17) 0.0813(9) Uani 1 1 d .
H3A H 1.3850 0.6066 1.0051 0.122 Uiso 1 1 calc R
H3B H 1.2921 0.5185 0.9960 0.122 Uiso 1 1 calc R
H3C H 1.3397 0.5773 1.0629 0.122 Uiso 1 1 calc R
C4 C 1.17018(19) 0.6837(3) 1.02327(13) 0.0611(7) Uani 1 1 d .
H4A H 1.1869 0.6718 1.0690 0.073 Uiso 1 1 calc R
H4B H 1.1428 0.6023 1.0043 0.073 Uiso 1 1 calc R
C5 C 1.09249(17) 0.7889(2) 1.00664(11) 0.0507(6) Uani 1 1 d .
C6 C 0.84076(19) 0.7481(3) 0.94029(14) 0.0598(7) Uani 1 1 d .
C7 C 0.7514(2) 0.8302(4) 0.9206(3) 0.1199(17) Uani 1 1 d .
H7A H 0.7225 0.8166 0.8763 0.180 Uiso 1 1 calc R
H7B H 0.7686 0.9204 0.9277 0.180 Uiso 1 1 calc R
H7C H 0.7058 0.8064 0.9450 0.180 Uiso 1 1 calc R
C8 C 0.46200(15) 0.1911(3) 0.82411(10) 0.0492(6) Uani 1 1 d .
C9 C 0.43910(18) 0.2926(3) 0.85984(12) 0.0691(8) Uani 1 1 d .
H9A H 0.4362 0.3768 0.8436 0.083 Uiso 1 1 calc R
C10 C 0.4201(2) 0.2730(5) 0.91975(14) 0.0917(13) Uani 1 1 d .
H10A H 0.4043 0.3436 0.9422 0.110 Uiso 1 1 calc R
C11 C 0.4247(2) 0.1507(5) 0.94527(14) 0.0972(14) Uani 1 1 d .
H11A H 0.4117 0.1375 0.9849 0.117 Uiso 1 1 calc R
C12 C 0.4487(2) 0.0476(4) 0.91156(13) 0.0865(11) Uani 1 1 d .
H12A H 0.4524 -0.0361 0.9284 0.104 Uiso 1 1 calc R
C13 C 0.46728(18) 0.0684(3) 0.85259(11) 0.0639(8) Uani 1 1 d .
H13A H 0.4841 -0.0028 0.8309 0.077 Uiso 1 1 calc R
C14 C 0.45567(15) 0.0906(2) 0.70672(9) 0.0439(5) Uani 1 1 d .
C15 C 0.36907(19) 0.0242(3) 0.70305(11) 0.0676(8) Uani 1 1 d .
H15A H 0.3327 0.0441 0.7323 0.081 Uiso 1 1 calc R
C16 C 0.3341(2) -0.0713(3) 0.65725(13) 0.0843(11) Uani 1 1 d .
H16A H 0.2759 -0.1138 0.6567 0.101 Uiso 1 1 calc R
C17 C 0.3852(3) -0.1025(3) 0.61340(13) 0.0772(9) Uani 1 1 d .
H17A H 0.3623 -0.1661 0.5830 0.093 Uiso 1 1 calc R
C18 C 0.4704(2) -0.0391(3) 0.61472(12) 0.0599(7) Uani 1 1 d .
H18A H 0.5056 -0.0589 0.5848 0.072 Uiso 1 1 calc R
C19 C 0.50467(17) 0.0551(2) 0.66056(10) 0.0469(5) Uani 1 1 d .
H19A H 0.5631 0.0965 0.6605 0.056 Uiso 1 1 calc R
C20 C 0.43924(15) 0.3396(2) 0.71575(9) 0.0453(5) Uani 1 1 d .
C21 C 0.34421(18) 0.3777(3) 0.71563(11) 0.0655(8) Uani 1 1 d .
H21A H 0.3117 0.3344 0.7421 0.079 Uiso 1 1 calc R
C22 C 0.2967(2) 0.4784(4) 0.67725(13) 0.0795(10) Uani 1 1 d .
H22A H 0.2336 0.5011 0.6786 0.095 Uiso 1 1 calc R
C23 C 0.3422(2) 0.5438(3) 0.63766(13) 0.0749(9) Uani 1 1 d .
H23A H 0.3105 0.6113 0.6123 0.090 Uiso 1 1 calc R
C24 C 0.4349(2) 0.5092(3) 0.63573(12) 0.0621(7) Uani 1 1 d .
H24A H 0.4666 0.5529 0.6089 0.075 Uiso 1 1 calc R
C25 C 0.48134(17) 0.4083(2) 0.67404(10) 0.0480(6) Uani 1 1 d .
H25A H 0.5440 0.3856 0.6716 0.058 Uiso 1 1 calc R
C26 C 0.61136(14) 0.2267(2) 0.77593(9) 0.0396(5) Uani 1 1 d .
C27 C 0.67303(16) 0.1199(3) 0.78299(11) 0.0511(6) Uani 1 1 d .
H27A H 0.6458 0.0373 0.7751 0.061 Uiso 1 1 calc R
C28 C 0.77401(18) 0.1309(3) 0.80138(12) 0.0651(8) Uani 1 1 d .
H28A H 0.8127 0.0567 0.8052 0.078 Uiso 1 1 calc R
C29 C 0.81609(18) 0.2510(3) 0.81385(12) 0.0652(8) Uani 1 1 d .
H29A H 0.8835 0.2593 0.8251 0.078 Uiso 1 1 calc R
C30 C 0.75812(18) 0.3592(3) 0.80971(11) 0.0593(7) Uani 1 1 d .
H30A H 0.7861 0.4411 0.8191 0.071 Uiso 1 1 calc R
C31 C 0.65764(17) 0.3463(2) 0.79151(10) 0.0495(6) Uani 1 1 d .
H31A H 0.6195 0.4208 0.7896 0.059 Uiso 1 1 calc R
C32 C 0.4793(5) 0.6988(5) 0.7852(2) 0.174(3) Uani 1 1 d .
H32A H 0.5416 0.7284 0.7806 0.261 Uiso 1 1 calc R
H32B H 0.4306 0.7627 0.7678 0.261 Uiso 1 1 calc R
H32C H 0.4633 0.6178 0.7630 0.261 Uiso 1 1 calc R
C33 C 0.4829(3) 0.6800(5) 0.8516(2) 0.1137(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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 112.2(3)
C1 N1 C3 109.9(2)
C2 N1 C3 108.3(2)
C1 N1 C4 108.8(2)
C2 N1 C4 110.3(2)
C3 N1 C4 107.2(2)
C5 N2 N3 122.7(2)
C6 N3 N2 116.3(2)
C20 B1 C14 103.22(16)
C20 B1 C8 113.70(19)
C14 B1 C8 111.89(18)
C20 B1 C26 112.15(18)
C14 B1 C26 112.14(18)
C8 B1 C26 104.03(16)
N1 C4 C5 115.2(2)
O1 C5 N2 123.2(2)
O1 C5 C4 124.5(2)
N2 C5 C4 112.2(2)
O2 C6 N3 120.9(3)
O2 C6 C7 124.0(3)
N3 C6 C7 115.1(3)
C9 C8 C13 115.2(2)
C9 C8 B1 123.1(2)
C13 C8 B1 121.4(2)
C8 C9 C10 122.3(3)
C11 C10 C9 120.4(3)
C10 C11 C12 119.0(3)
C11 C12 C13 120.0(4)
C12 C13 C8 123.1(3)
C15 C14 C19 114.5(2)
C15 C14 B1 123.0(2)
C19 C14 B1 122.23(19)
C14 C15 C16 122.8(3)
C17 C16 C15 120.2(3)
C16 C17 C18 119.1(3)
C17 C18 C19 120.1(3)
C18 C19 C14 123.2(2)
C25 C20 C21 114.8(2)
C25 C20 B1 122.50(19)
C21 C20 B1 122.4(2)
C22 C21 C20 122.2(3)
C23 C22 C21 120.5(3)
C22 C23 C24 119.4(3)
C23 C24 C25 119.6(3)
C20 C25 C24 123.5(2)
C27 C26 C31 115.0(2)
C27 C26 B1 122.7(2)
C31 C26 B1 122.2(2)
C26 C27 C28 122.9(2)
C29 C28 C27 119.8(3)
C28 C29 C30 119.5(2)
C29 C30 C31 119.8(3)
C30 C31 C26 122.9(2)
N4 C33 C32 177.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.478(3)
N1 C2 1.480(3)
N1 C3 1.497(3)
N1 C4 1.503(3)
N2 C5 1.328(3)
N2 N3 1.372(3)
N3 C6 1.340(3)
N4 C33 1.117(6)
O1 C5 1.218(3)
O2 C6 1.212(3)
B1 C20 1.642(3)
B1 C14 1.646(3)
B1 C8 1.648(3)
B1 C26 1.648(3)
C4 C5 1.520(3)
C6 C7 1.494(4)
C8 C9 1.382(4)
C8 C13 1.396(4)
C9 C10 1.403(4)
C10 C11 1.366(6)
C11 C12 1.374(6)
C12 C13 1.383(4)
C14 C15 1.387(3)
C14 C19 1.396(3)
C15 C16 1.399(4)
C16 C17 1.364(5)
C17 C18 1.364(4)
C18 C19 1.388(3)
C20 C25 1.389(3)
C20 C21 1.399(3)
C21 C22 1.394(4)
C22 C23 1.367(5)
C23 C24 1.369(4)
C24 C25 1.390(3)
C26 C27 1.385(3)
C26 C31 1.394(3)
C27 C28 1.393(3)
C28 C29 1.367(4)
C29 C30 1.370(4)
C30 C31 1.387(3)
C32 C33 1.442(7)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651542 ChemSpider
