#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/66/2216602.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_2216602
loop_
_publ_author_name
'Zhang, Dan'
'Harrington, Laura E.'
'Tanaka, Hiroo'
'Pelton, Robert'
_publ_section_title
;
 [3-(Propenamido)phenyl]boronic acid
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4628
_journal_paper_doi               10.1107/S1600536807055389
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H10 B N O3'
_chemical_formula_moiety         'C9 H10 B N O3'
_chemical_formula_sum            'C9 H10 B N O3'
_chemical_formula_weight         190.99
_chemical_name_systematic
;
[3-(Propenamido)phenyl]boronic acid
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   18.626(4)
_cell_length_b                   42.112(8)
_cell_length_c                   5.0536(10)
_cell_measurement_reflns_used    2853
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.39
_cell_volume                     3963.9(14)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics
'SHELXTL (Bruker, 2000) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14806
_diffrn_reflns_theta_full        30.47
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(face correction with APEX2; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.5557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                1279
_reflns_number_total             1657
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            kj2069.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3963.9(13)
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               2216602
_cod_database_fobs_code          2216602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.34232(7) 0.11569(4) 1.1454(4) 0.0653(5) Uani d . 1 . .
O O2 0.43076(12) 0.01158(6) 0.3738(4) 0.0779(6) Uani d . 1 . .
H H2A 0.466(3) 0.0024(17) 0.394(16) 0.082(10) Uiso d P 0.50 A 1
H H2B 0.413(4) 0.0131(15) 0.237(17) 0.082(10) Uiso d P 0.50 B 2
O O3 0.43531(9) 0.01566(4) 0.8312(3) 0.0569(4) Uani d . 1 . .
H H3A 0.414(4) 0.0220(15) 0.944(17) 0.082(10) Uiso d P 0.50 C 1
H H3B 0.478(3) 0.0072(14) 0.827(14) 0.082(10) Uiso d P 0.50 D 2
N N1 0.23312(9) 0.10547(4) 0.9628(3) 0.0476(4) Uani d . 1 . .
H H1A 0.1859(16) 0.1131(6) 0.949(6) 0.072(8) Uiso d . 1 . .
B B1 0.39944(13) 0.02160(6) 0.6027(5) 0.0469(5) Uani d . 1 . .
C C1 0.24915(10) 0.08023(4) 0.7901(4) 0.0442(4) Uani d . 1 . .
C C2 0.19502(12) 0.07111(5) 0.6107(5) 0.0567(5) Uani d . 1 . .
H H2 0.1493(13) 0.0830(5) 0.624(6) 0.059(6) Uiso d . 1 . .
C C3 0.20685(14) 0.04743(6) 0.4318(5) 0.0633(6) Uani d . 1 . .
H H3 0.1704(15) 0.0419(6) 0.324(7) 0.068(7) Uiso d . 1 . .
C C4 0.27236(13) 0.03202(5) 0.4223(4) 0.0543(5) Uani d . 1 . .
H H4 0.2783(13) 0.0162(6) 0.288(6) 0.060(7) Uiso d . 1 . .
C C5 0.32638(10) 0.03966(4) 0.6037(4) 0.0447(4) Uani d . 1 . .
C C6 0.31372(10) 0.06372(5) 0.7880(4) 0.0433(4) Uani d . 1 . .
H H6 0.3479(12) 0.0696(5) 0.914(5) 0.055(6) Uiso d . 1 . .
C C7 0.27804(10) 0.12142(5) 1.1262(4) 0.0478(4) Uani d . 1 . .
C C8 0.24262(14) 0.14649(6) 1.2856(6) 0.0646(6) Uani d . 1 . .
H H8 0.1923(18) 0.1488(7) 1.258(8) 0.085(9) Uiso d . 1 . .
C C9 0.2770(2) 0.16236(8) 1.4653(8) 0.0938(11) Uani d . 1 . .
H H9A 0.2548(17) 0.1772(8) 1.613(9) 0.101(10) Uiso d . 1 . .
H H9B 0.322(2) 0.1570(8) 1.511(9) 0.105(12) Uiso d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0357(7) 0.0729(9) 0.0873(12) 0.0017(6) -0.0151(8) -0.0233(9)
O2 0.0824(15) 0.1155(17) 0.0359(9) 0.0226(11) 0.0051(9) -0.0134(10)
O3 0.0593(10) 0.0778(11) 0.0334(7) 0.0152(8) -0.0019(6) -0.0005(7)
N1 0.0334(8) 0.0568(9) 0.0526(9) 0.0036(7) -0.0099(7) -0.0050(8)
B1 0.0551(12) 0.0549(11) 0.0307(8) 0.0020(9) 0.0008(8) -0.0002(9)
C1 0.0394(9) 0.0505(10) 0.0427(9) -0.0035(8) -0.0090(7) 0.0036(8)
C2 0.0463(11) 0.0635(12) 0.0602(13) -0.0005(10) -0.0215(10) -0.0013(11)
C3 0.0607(13) 0.0686(14) 0.0606(13) -0.0068(11) -0.0281(11) -0.0065(11)
C4 0.0648(13) 0.0559(11) 0.0421(10) -0.0038(10) -0.0128(9) -0.0034(9)
C5 0.0507(10) 0.0511(10) 0.0324(8) -0.0022(8) -0.0017(7) 0.0052(8)
C6 0.0380(9) 0.0550(11) 0.0370(9) -0.0014(8) -0.0066(7) -0.0001(7)
C7 0.0381(9) 0.0530(10) 0.0522(10) -0.0016(8) -0.0076(8) -0.0007(9)
C8 0.0525(13) 0.0653(13) 0.0760(17) 0.0114(11) -0.0125(12) -0.0159(12)
C9 0.081(2) 0.097(2) 0.104(3) 0.0237(17) -0.0317(18) -0.049(2)
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
B1 O2 H2A 114(6)
B1 O2 H2B 123(6)
H2A O2 H2B 122(8)
B1 O3 H3A 109(6)
B1 O3 H3B 120(5)
H3A O3 H3B 131(7)
C7 N1 C1 128.46(17)
C7 N1 H1A 117.1(18)
C1 N1 H1A 114.2(18)
O3 B1 O2 117.0(2)
O3 B1 C5 121.1(2)
O2 B1 C5 121.8(2)
C6 C1 N1 124.49(16)
C6 C1 C2 118.57(19)
N1 C1 C2 116.93(18)
C3 C2 C1 120.7(2)
C3 C2 H2 123.6(16)
C1 C2 H2 115.7(15)
C2 C3 C4 120.6(2)
C2 C3 H3 117.8(18)
C4 C3 H3 121.6(17)
C3 C4 C5 120.3(2)
C3 C4 H4 116.9(15)
C5 C4 H4 122.9(15)
C6 C5 C4 118.86(18)
C6 C5 B1 120.24(17)
C4 C5 B1 120.90(19)
C1 C6 C5 120.95(16)
C1 C6 H6 117.0(14)
C5 C6 H6 122.0(14)
O1 C7 N1 123.7(2)
O1 C7 C8 122.2(2)
N1 C7 C8 114.19(18)
C9 C8 C7 121.8(3)
C9 C8 H8 122(2)
C7 C8 H8 116(2)
C8 C9 H9A 127.2(19)
C8 C9 H9B 121(2)
H9A C9 H9B 109(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.225(2)
O2 B1 1.363(3)
O2 H2A 0.76(7)
O2 H2B 0.77(8)
O3 B1 1.357(3)
O3 H3A 0.74(8)
O3 H3B 0.87(5)
N1 C7 1.354(3)
N1 C1 1.407(3)
N1 H1A 0.94(3)
B1 C5 1.559(3)
C1 C6 1.389(3)
C1 C2 1.409(3)
C2 C3 1.364(4)
C2 H2 0.99(2)
C3 C4 1.383(4)
C3 H3 0.90(3)
C4 C5 1.399(3)
C4 H4 0.96(3)
C5 C6 1.396(3)
C6 H6 0.93(3)
C7 C8 1.483(3)
C8 C9 1.297(4)
C8 H8 0.95(3)
C9 H9A 1.06(4)
C9 H9B 0.89(4)
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
_geom_hbond_publ_flag
O2 H2A O2 2_655 0.77(7) 2.02(7) 2.759(3) 163(7) yes
O2 H2B O3 1_554 0.77(8) 2.10(9) 2.748(3) 143(7) yes
O3 H3A O2 1_556 0.75(8) 2.24(8) 2.748(3) 126(7) yes
O3 H3B O3 2_655 0.87(5) 1.88(5) 2.746(3) 173(6) yes
N1 H1A O1 11_454 0.93(3) 1.98(3) 2.911(3) 172(2) yes
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
C7 N1 C1 C6 10.7(3)
C7 N1 C1 C2 -170.2(2)
C6 C1 C2 C3 -2.6(3)
N1 C1 C2 C3 178.2(2)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 2.6(4)
C3 C4 C5 C6 -2.0(3)
C3 C4 C5 B1 177.6(2)
O3 B1 C5 C6 34.3(3)
O2 B1 C5 C6 -144.5(2)
O3 B1 C5 C4 -145.3(2)
O2 B1 C5 C4 35.9(3)
N1 C1 C6 C5 -177.70(18)
C2 C1 C6 C5 3.2(3)
C4 C5 C6 C1 -0.9(3)
B1 C5 C6 C1 179.45(19)
C1 N1 C7 O1 0.3(3)
C1 N1 C7 C8 -178.9(2)
O1 C7 C8 C9 -4.2(4)
N1 C7 C8 C9 174.9(3)
