#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/83/2218304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218304
loop_
_publ_author_name
'Klis, Tomasz'
'Serwatowski, Janusz'
_publ_section_title
;
 tert-Butyl 2-(dihydroxyboryl)pyrrole-1-carboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1054
_journal_paper_doi               10.1107/S1600536808013482
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H14 B N O4'
_chemical_formula_moiety         'C9 H14 B N O4'
_chemical_formula_sum            'C9 H14 B N O4'
_chemical_formula_weight         211.02
_chemical_name_systematic
;
tert-Butyl 2-(dihydroxyboryl)pyrrole-1-carboxylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.9179(12)
_cell_length_b                   9.5885(7)
_cell_length_c                   17.5811(15)
_cell_measurement_reflns_used    19290
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.71
_cell_measurement_theta_min      2.80
_cell_volume                     2177.7(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2005)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2005)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2005)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Kuma KM4 CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19290
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        2
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction 2005)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.0033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0306
_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)+(0.0461P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                1911
_reflns_number_total             2713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2173.cif
_cod_data_source_block           I
_cod_database_code               2218304
_cod_database_fobs_code          2218304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_occupancy
O O1 0.54350(6) 0.63771(7) 0.45212(4) 0.02586(19) Uani d 1
O O2 0.40336(6) 0.64180(8) 0.53731(4) 0.02619(19) Uani d 1
O O3 0.60617(5) 0.83554(7) 0.36263(4) 0.02260(18) Uani d 1
O O4 0.56150(5) 1.04637(7) 0.31656(4) 0.02186(18) Uani d 1
N N1 0.46192(6) 0.95162(8) 0.40642(4) 0.01800(19) Uani d 1
C C1 0.42176(8) 0.85423(10) 0.45945(5) 0.0187(2) Uani d 1
C C2 0.33504(8) 0.91604(11) 0.48868(6) 0.0223(2) Uani d 1
C C3 0.32126(8) 1.05007(11) 0.45569(6) 0.0242(2) Uani d 1
C C4 0.39900(8) 1.06957(10) 0.40571(6) 0.0218(2) Uani d 1
C C5 0.54985(8) 0.93691(9) 0.36119(5) 0.0186(2) Uani d 1
C C6 0.64575(8) 1.04984(10) 0.25803(5) 0.0225(2) Uani d 1
C C7 0.63032(10) 0.93008(12) 0.20274(6) 0.0285(3) Uani d 1
C C8 0.75028(9) 1.04896(12) 0.29709(6) 0.0269(2) Uani d 1
C C9 0.62477(10) 1.18889(12) 0.22011(7) 0.0304(3) Uani d 1
B B1 0.46066(9) 0.70564(12) 0.48297(6) 0.0204(2) Uani d 1
H H1O 0.5763(11) 0.6964(15) 0.4187(8) 0.056(4) Uiso d 1
H H2O 0.4234(12) 0.5504(17) 0.5442(8) 0.060(5) Uiso d 1
H H2 0.2915(8) 0.8741(11) 0.5269(5) 0.018(2) Uiso d 1
H H3 0.2680(9) 1.1122(12) 0.4668(6) 0.028(3) Uiso d 1
H H4 0.4168(8) 1.1463(11) 0.3729(6) 0.020(3) Uiso d 1
H H7A 0.5580(11) 0.9321(12) 0.1830(7) 0.038(3) Uiso d 1
H H7B 0.6429(9) 0.8387(12) 0.2253(6) 0.029(3) Uiso d 1
H H7C 0.6788(9) 0.9424(11) 0.1603(6) 0.029(3) Uiso d 1
H H8A 0.7576(9) 1.1342(13) 0.3317(7) 0.038(3) Uiso d 1
H H8B 0.7629(9) 0.9613(12) 0.3252(6) 0.031(3) Uiso d 1
H H8C 0.8046(10) 1.0547(12) 0.2579(7) 0.036(3) Uiso d 1
H H9A 0.6288(8) 1.2649(12) 0.2567(7) 0.034(3) Uiso d 1
H H9B 0.5551(10) 1.1878(13) 0.1981(6) 0.040(3) Uiso d 1
H H9C 0.6768(9) 1.2037(12) 0.1802(7) 0.039(3) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
B1 O1 H1O 108.9(9)
B1 O2 H2O 111.6(9)
C5 O4 C6 120.61(7)
C4 N1 C5 123.55(8)
C4 N1 C1 109.10(8)
C5 N1 C1 127.35(8)
C2 C1 N1 105.15(8)
C2 C1 B1 123.90(9)
N1 C1 B1 130.94(9)
C1 C2 C3 109.95(9)
C1 C2 H2 124.0(6)
C3 C2 H2 126.0(6)
C4 C3 C2 107.35(9)
C4 C3 H3 126.8(7)
C2 C3 H3 125.9(7)
C3 C4 N1 108.44(9)
C3 C4 H4 132.4(6)
N1 C4 H4 119.1(6)
O3 C5 O4 125.51(9)
O3 C5 N1 123.88(8)
O4 C5 N1 110.60(8)
O4 C6 C8 109.64(8)
O4 C6 C9 101.06(8)
C8 C6 C9 111.34(9)
O4 C6 C7 109.13(8)
C8 C6 C7 113.78(9)
C9 C6 C7 111.13(9)
C6 C7 H7A 109.4(7)
C6 C7 H7B 113.4(6)
H7A C7 H7B 108.4(10)
C6 C7 H7C 108.2(6)
H7A C7 H7C 109.3(9)
H7B C7 H7C 108.1(9)
C6 C8 H8A 110.3(7)
C6 C8 H8B 112.2(7)
H8A C8 H8B 111.5(9)
C6 C8 H8C 108.5(7)
H8A C8 H8C 107.8(9)
H8B C8 H8C 106.2(9)
C6 C9 H9A 111.0(7)
C6 C9 H9B 109.2(7)
H9A C9 H9B 108.6(10)
C6 C9 H9C 108.6(7)
H9A C9 H9C 109.1(10)
H9B C9 H9C 110.4(9)
O2 B1 O1 119.54(10)
O2 B1 C1 114.96(9)
O1 B1 C1 125.49(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 B1 1.3652(13)
O1 H1O 0.917(15)
O2 B1 1.3547(13)
O2 H2O 0.922(16)
O3 C5 1.2143(11)
O4 C5 1.3191(11)
O4 C6 1.4981(12)
N1 C4 1.3928(12)
N1 C5 1.3937(12)
N1 C1 1.4178(12)
C1 C2 1.3676(14)
C1 B1 1.5665(15)
C2 C3 1.4211(15)
C2 H2 0.964(10)
C3 C4 1.3474(15)
C3 H3 0.931(12)
C4 H4 0.963(10)
C6 C8 1.5149(15)
C6 C9 1.5151(14)
C6 C7 1.5176(14)
C7 H7A 0.996(13)
C7 H7B 0.976(11)
C7 H7C 0.981(12)
C8 H8A 1.023(13)
C8 H8B 0.989(12)
C8 H8C 0.985(13)
C9 H9A 0.973(12)
C9 H9B 0.980(13)
C9 H9C 0.983(12)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O O3 . 0.917(15) 1.704(15) 2.5941(10) 162.9(13)
O2 H2O O1 5_666 0.922(16) 1.855(17) 2.7728(11) 173.7(13)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 N1 C1 C2 0.54(10)
C5 N1 C1 C2 -179.63(8)
C4 N1 C1 B1 179.79(9)
C5 N1 C1 B1 -0.38(15)
N1 C1 C2 C3 -0.70(10)
B1 C1 C2 C3 179.99(9)
C1 C2 C3 C4 0.62(11)
C2 C3 C4 N1 -0.26(11)
C5 N1 C4 C3 179.99(8)
C1 N1 C4 C3 -0.17(10)
C6 O4 C5 O3 3.95(14)
C6 O4 C5 N1 -174.99(7)
C4 N1 C5 O3 178.49(9)
C1 N1 C5 O3 -1.32(14)
C4 N1 C5 O4 -2.55(12)
C1 N1 C5 O4 177.64(8)
C5 O4 C6 C8 -64.93(11)
C5 O4 C6 C9 177.47(8)
C5 O4 C6 C7 60.31(11)
C2 C1 B1 O2 -1.97(14)
N1 C1 B1 O2 178.91(9)
C2 C1 B1 O1 176.28(10)
N1 C1 B1 O1 -2.85(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2016073
