#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:44:30 +0100 (lun 21 de mar de 2016) $
#$Revision: 178441 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/62/4026262.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_4026262
loop_
_publ_author_name
'Jing Sun'
'Michael T. Perfetti'
'Webster L. Santos'
_publ_section_title
;
 A Method for the Deprotection of Alkylpinacolyl Boronate Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3571
_journal_page_last               3575
_journal_paper_doi               10.1021/jo200250y
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C8 H16 B N O4'
_chemical_formula_sum            'C8 H16 B N O4'
_chemical_formula_weight         201.03
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                   22.3967(9)
_cell_length_b                   4.7980(2)
_cell_length_c                   9.4977(4)
_cell_measurement_reflns_used    3521
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4246
_cell_measurement_theta_min      3.4615
_cell_volume                     1020.62(7)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_publication_material
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_solution
'SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.2265
_diffrn_detector_type            'Oxford Diffraction Atlas CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.1213279707
_diffrn_orient_matrix_UB_12      -0.0067373282
_diffrn_orient_matrix_UB_13      0.0178094800
_diffrn_orient_matrix_UB_21      -0.0800613413
_diffrn_orient_matrix_UB_22      -0.0145222436
_diffrn_orient_matrix_UB_23      -0.0259739354
_diffrn_orient_matrix_UB_31      0.0269336080
_diffrn_orient_matrix_UB_32      -0.0730284900
_diffrn_orient_matrix_UB_33      0.0035169359
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8805
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40
_diffrn_source_voltage           50
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1248
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0368
_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)+(0.0460P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0792
_reflns_number_gt                1061
_reflns_number_total             1248
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200250y_si_001.cif
_cod_data_source_block           cs1473
_cod_database_code               4026262
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
B1 B 0.40884(11) 0.5782(5) 0.0845(3) 0.0161(5) Uani 1 1 d .
C1 C 0.38362(11) 0.8384(5) 0.3032(2) 0.0219(5) Uani 1 1 d .
H1A H 0.3512 0.9716 0.2814 0.026 Uiso 1 1 calc R
H1B H 0.4013 0.8872 0.3955 0.026 Uiso 1 1 calc R
C2 C 0.36071(11) 0.5402(5) 0.3030(2) 0.0237(6) Uani 1 1 d .
H2A H 0.3883 0.4162 0.3549 0.028 Uiso 1 1 calc R
H2B H 0.3207 0.5294 0.3471 0.028 Uiso 1 1 calc R
C3 C 0.49165(10) 0.7638(5) 0.2362(2) 0.0228(5) Uani 1 1 d .
H3A H 0.4912 0.6726 0.3297 0.027 Uiso 1 1 calc R
H3B H 0.5176 0.9308 0.2404 0.027 Uiso 1 1 calc R
C4 C 0.51252(11) 0.5634(5) 0.1225(2) 0.0225(5) Uani 1 1 d .
H4A H 0.5255 0.6660 0.0374 0.027 Uiso 1 1 calc R
H4B H 0.5461 0.4476 0.1567 0.027 Uiso 1 1 calc R
C5 C 0.39453(10) 0.6774(5) -0.0734(2) 0.0158(5) Uani 1 1 d .
H5A H 0.4304 0.7721 -0.1113 0.019 Uiso 1 1 calc R
H5B H 0.3875 0.5097 -0.1318 0.019 Uiso 1 1 calc R
C6 C 0.34143(10) 0.8717(5) -0.0907(2) 0.0187(5) Uani 1 1 d .
H6A H 0.3044 0.7679 -0.0686 0.022 Uiso 1 1 calc R
H6B H 0.3450 1.0260 -0.0220 0.022 Uiso 1 1 calc R
C7 C 0.33620(9) 0.9927(5) -0.2362(2) 0.0176(5) Uani 1 1 d .
C8 C 0.28190(11) 1.2956(6) -0.3829(3) 0.0299(6) Uani 1 1 d .
H8A H 0.3153 1.4253 -0.3949 0.045 Uiso 1 1 calc R
H8B H 0.2442 1.3990 -0.3857 0.045 Uiso 1 1 calc R
H8C H 0.2825 1.1576 -0.4590 0.045 Uiso 1 1 calc R
N1 N 0.42995(8) 0.8383(4) 0.19000(19) 0.0172(4) Uani 1 1 d .
H1 H 0.4299 1.0069 0.1417 0.021 Uiso 1 1 calc R
O1 O 0.35784(7) 0.4638(3) 0.15840(15) 0.0204(4) Uani 1 1 d .
O2 O 0.46178(7) 0.3959(3) 0.09295(17) 0.0193(4) Uani 1 1 d .
O3 O 0.37104(7) 0.9598(4) -0.33158(16) 0.0266(4) Uani 1 1 d .
O4 O 0.28742(7) 1.1550(4) -0.24872(16) 0.0265(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0229(12) 0.0108(12) 0.0144(12) 0.0002(11) -0.0031(11) -0.0022(10)
C1 0.0334(14) 0.0180(13) 0.0144(11) 0.0011(9) 0.0019(9) 0.0025(11)
C2 0.0330(13) 0.0214(14) 0.0167(12) 0.0040(10) 0.0041(10) -0.0024(11)
C3 0.0284(12) 0.0213(12) 0.0189(11) 0.0010(10) -0.0067(10) -0.0053(10)
C4 0.0233(12) 0.0256(14) 0.0185(11) 0.0039(10) -0.0044(9) -0.0001(11)
C5 0.0198(10) 0.0153(12) 0.0125(10) 0.0013(9) 0.0027(8) -0.0018(9)
C6 0.0208(11) 0.0205(12) 0.0148(11) 0.0014(10) 0.0013(9) 0.0005(10)
C7 0.0169(10) 0.0184(11) 0.0174(12) 0.0017(10) -0.0029(9) -0.0024(9)
C8 0.0263(13) 0.0409(16) 0.0225(12) 0.0130(12) -0.0009(10) 0.0087(12)
N1 0.0260(9) 0.0128(10) 0.0128(8) 0.0025(8) -0.0018(8) -0.0026(8)
O1 0.0249(8) 0.0209(9) 0.0153(8) 0.0020(7) 0.0003(7) -0.0058(7)
O2 0.0224(8) 0.0162(7) 0.0191(8) 0.0015(7) -0.0022(6) 0.0005(7)
O3 0.0281(8) 0.0364(11) 0.0152(9) 0.0041(8) 0.0034(7) 0.0083(8)
O4 0.0220(8) 0.0386(10) 0.0189(8) 0.0107(8) 0.0020(7) 0.0080(7)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 0 0.1574 -1.0003 -0.0067 0.0043 0.1215 0.0801 -0.0264
1 0 0 0.1574 1.0003 0.0067 -0.0043 -0.1215 -0.0801 0.0264
0 -1 0 0.0741 0.0022 -0.9987 -0.0012 0.0064 0.0144 0.0730
0 1 0 0.0741 -0.0022 0.9987 0.0012 -0.0064 -0.0144 -0.0730
0 0 -1 0.0104 0.0004 0.0003 -0.9994 -0.0178 0.0259 -0.0035
0 0 1 0.0104 -0.0004 -0.0003 0.9994 0.0178 -0.0259 0.0035
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 B1 O2 112.49(18)
O1 B1 C5 114.06(18)
O2 B1 C5 112.77(19)
O1 B1 N1 102.45(18)
O2 B1 N1 100.53(16)
C5 B1 N1 113.32(18)
N1 C1 C2 103.46(19)
O1 C2 C1 105.04(18)
N1 C3 C4 103.14(18)
O2 C4 C3 104.62(18)
C6 C5 B1 116.03(17)
C7 C6 C5 113.40(18)
O3 C7 O4 122.3(2)
O3 C7 C6 126.1(2)
O4 C7 C6 111.59(19)
C3 N1 C1 115.54(17)
C3 N1 B1 105.06(16)
C1 N1 B1 103.64(16)
C2 O1 B1 109.54(17)
C4 O2 B1 108.57(16)
C7 O4 C8 114.63(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 O1 1.449(3)
B1 O2 1.476(3)
B1 C5 1.606(3)
B1 N1 1.669(3)
C1 N1 1.494(3)
C1 C2 1.520(3)
C2 O1 1.423(3)
C3 N1 1.493(3)
C3 C4 1.520(3)
C4 O2 1.420(3)
C5 C6 1.520(3)
C6 C7 1.503(3)
C7 O3 1.206(3)
C7 O4 1.347(3)
C8 O4 1.447(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.93 2.05 2.918(2) 154.5 1_565
