##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[2,2'-Iminodiethanolato(2-)-\k^3^<i>O</i>,<i>N</i>,<i>O</i>'][4-
(methoxycarbonylmethyl)phenyl]boron
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H18 B N O4'
_chemical_formula_sum     'C13 H18 B N O4'
_chemical_formula_iupac     'C13 H18 B N O4'
_chemical_formula_weight     263.10
_chemical_melting_point_gt     452
_chemical_melting_point_lt     453
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x+1/2, -y, z+1/2'
_cell_length_a     8.3776(11)
_cell_length_b     8.9269(11)
_cell_length_c     17.369(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1299.0(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5108
_cell_measurement_theta_min     2.5654
_cell_measurement_theta_max     30.5672
_cell_measurement_temperature     153(2)
_exptl_crystal_description     'Platelet'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.09
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.345
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_absorpt_correction_T_min     0.9852
_exptl_absorpt_correction_T_max     0.9968
_exptl_special_details
;
;
_diffrn_ambient_temperature     153(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite - Rigaku SHINE'
_diffrn_measurement_device_type     'Rigaku Saturn'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     14.63
_diffrn_reflns_number     16363
_diffrn_reflns_av_R_equivalents     0.0370
_diffrn_reflns_av_sigmaI/netI     0.0168
_diffrn_reflns_theta_min     2.57
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
The crystal was a weak anomalous scatterer collected with Mo <i>K</i>\a
radiation. Friedel mates were merged (MERG 4) and the absolute configuration
was not determined.
;
_reflns_number_total     1725
_reflns_number_gt     1707
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0440
_refine_ls_R_factor_gt     0.0434
_refine_ls_wR_factor_gt     0.1120
_refine_ls_wR_factor_ref     0.1123
_refine_ls_goodness_of_fit_ref     1.172
_refine_ls_restrained_S_all     1.172
_refine_ls_number_reflns     1725
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.4126P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.200
_refine_diff_density_min     -0.223
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrystalClear (Rigaku, 2002)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2002)'
_computing_data_reduction     'CrystalClear (Rigaku, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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 1.00908(19) 0.47529(18) 0.35582(9) 0.0281(4) Uani d . 1 . .
    O O2 0.85897(19) 0.47478(17) 0.23631(9) 0.0268(4) Uani d . 1 . .
    O O3 0.5232(2) -0.2735(2) 0.39057(11) 0.0422(5) Uani d . 1 . .
    O O4 0.6510(3) -0.2494(3) 0.50205(13) 0.0617(7) Uani d . 1 . .
    N N1 1.0730(2) 0.2952(2) 0.25504(10) 0.0249(4) Uani d . 1 . .
    H H1 1.0599 0.1919 0.2577 0.030 Uiso calc R 1 . .
    C C1 0.7998(3) 0.2734(2) 0.34181(12) 0.0243(4) Uani d . 1 . .
    C C2 0.6576(3) 0.2247(3) 0.30806(13) 0.0253(4) Uani d . 1 . .
    H H2 0.6285 0.2624 0.2589 0.030 Uiso calc R 1 . .
    C C3 0.5568(3) 0.1220(3) 0.34475(13) 0.0261(5) Uani d . 1 . .
    H H3 0.4626 0.0888 0.3195 0.031 Uiso calc R 1 . .
    C C4 0.5932(3) 0.0679(3) 0.41775(13) 0.0263(5) Uani d . 1 . .
    C C5 0.7326(3) 0.1174(3) 0.45272(13) 0.0296(5) Uani d . 1 . .
    H H5 0.7589 0.0827 0.5028 0.035 Uiso calc R 1 . .
    C C6 0.8342(3) 0.2173(3) 0.41551(13) 0.0276(5) Uani d . 1 . .
    H H6 0.9294 0.2482 0.4406 0.033 Uiso calc R 1 . .
    C C7 1.1685(3) 0.4963(3) 0.33084(14) 0.0302(5) Uani d . 1 . .
    H H7A 1.2382 0.5254 0.3744 0.036 Uiso calc R 1 . .
    H H7B 1.1743 0.5747 0.2906 0.036 Uiso calc R 1 . .
    C C8 1.2172(3) 0.3441(3) 0.29856(15) 0.0313(5) Uani d . 1 . .
    H H8A 1.3108 0.3534 0.2641 0.038 Uiso calc R 1 . .
    H H8B 1.2427 0.2729 0.3405 0.038 Uiso calc R 1 . .
    C C9 0.8982(3) 0.4085(3) 0.16438(13) 0.0283(5) Uani d . 1 . .
    H H9A 0.8939 0.4839 0.1226 0.034 Uiso calc R 1 . .
    H H9B 0.8231 0.3263 0.1520 0.034 Uiso calc R 1 . .
    C C10 1.0671(3) 0.3484(3) 0.17388(14) 0.0297(5) Uani d . 1 . .
    H H10A 1.0875 0.2650 0.1376 0.036 Uiso calc R 1 . .
    H H10B 1.1469 0.4283 0.1649 0.036 Uiso calc R 1 . .
    C C11 0.4878(3) -0.0470(3) 0.45767(13) 0.0287(5) Uani d . 1 . .
    H H11A 0.4717 -0.0173 0.5120 0.034 Uiso calc R 1 . .
    H H11B 0.3821 -0.0498 0.4323 0.034 Uiso calc R 1 . .
    C C12 0.5624(3) -0.1999(3) 0.45463(15) 0.0330(5) Uani d . 1 . .
    C C13 0.5926(4) -0.4222(3) 0.3835(2) 0.0499(8) Uani d . 1 . .
    H H13A 0.7093 -0.4143 0.3831 0.060 Uiso calc R 1 . .
    H H13B 0.5563 -0.4686 0.3354 0.060 Uiso calc R 1 . .
    H H13C 0.5589 -0.4840 0.4272 0.060 Uiso calc R 1 . .
    B B1 0.9234(3) 0.3847(3) 0.30025(14) 0.0236(5) Uani 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 0.0291(8) 0.0257(8) 0.0296(8) -0.0045(7) 0.0027(6) -0.0029(7)
    O2 0.0318(8) 0.0203(7) 0.0283(8) 0.0029(7) 0.0023(7) 0.0014(6)
    O3 0.0412(10) 0.0352(10) 0.0503(10) 0.0057(9) -0.0049(9) -0.0132(9)
    O4 0.0875(17) 0.0522(12) 0.0453(11) 0.0243(14) -0.0164(12) 0.0011(9)
    N1 0.0271(9) 0.0181(8) 0.0295(9) 0.0004(8) 0.0027(8) 0.0024(8)
    C1 0.0254(10) 0.0195(10) 0.0279(10) 0.0014(9) 0.0055(8) -0.0020(9)
    C2 0.0263(10) 0.0228(10) 0.0268(10) 0.0030(9) 0.0023(9) 0.0005(9)
    C3 0.0232(10) 0.0234(10) 0.0318(11) 0.0010(9) 0.0011(9) -0.0018(9)
    C4 0.0289(10) 0.0213(10) 0.0286(10) 0.0009(9) 0.0075(9) -0.0026(9)
    C5 0.0360(12) 0.0291(11) 0.0236(10) -0.0050(10) 0.0014(10) 0.0013(9)
    C6 0.0282(10) 0.0270(11) 0.0276(10) -0.0031(10) 0.0000(9) -0.0030(9)
    C7 0.0285(11) 0.0286(12) 0.0334(12) -0.0054(10) -0.0020(9) 0.0032(10)
    C8 0.0262(11) 0.0284(12) 0.0393(13) -0.0005(10) -0.0021(10) 0.0054(10)
    C9 0.0349(12) 0.0233(11) 0.0266(11) -0.0002(10) -0.0020(9) 0.0003(9)
    C10 0.0347(12) 0.0259(11) 0.0285(11) 0.0016(10) 0.0062(10) 0.0010(9)
    C11 0.0308(11) 0.0261(11) 0.0291(11) -0.0023(9) 0.0051(9) -0.0008(9)
    C12 0.0345(12) 0.0316(12) 0.0330(11) -0.0013(11) 0.0057(10) 0.0010(10)
    C13 0.0444(15) 0.0340(14) 0.071(2) 0.0026(13) 0.0060(15) -0.0162(15)
    B1 0.0261(12) 0.0188(11) 0.0258(11) 0.0004(10) 0.0020(10) -0.0009(9)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . 1.417(3) ?
    O1 B1 . 1.449(3) ?
    O2 C9 . 1.421(3) ?
    O2 B1 . 1.474(3) ?
    O3 C12 . 1.333(3) ?
    O3 C13 . 1.455(4) ?
    O4 C12 . 1.193(3) ?
    N1 C10 . 1.488(3) ?
    N1 C8 . 1.491(3) ?
    N1 B1 . 1.681(3) ?
    N1 H1 . 0.9300 ?
    C1 C2 . 1.397(3) ?
    C1 C6 . 1.405(3) ?
    C1 B1 . 1.607(3) ?
    C2 C3 . 1.400(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.391(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.388(3) ?
    C4 C11 . 1.520(3) ?
    C5 C6 . 1.392(3) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.525(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.523(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.502(3) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7 O1 B1 . . 109.67(18) ?
    C9 O2 B1 . . 110.55(17) ?
    C12 O3 C13 . . 114.9(2) ?
    C10 N1 C8 . . 114.44(19) ?
    C10 N1 B1 . . 105.44(17) ?
    C8 N1 B1 . . 103.17(17) ?
    C10 N1 H1 . . 111.1 ?
    C8 N1 H1 . . 111.1 ?
    B1 N1 H1 . . 111.1 ?
    C2 C1 C6 . . 116.5(2) ?
    C2 C1 B1 . . 123.6(2) ?
    C6 C1 B1 . . 119.9(2) ?
    C1 C2 C3 . . 121.8(2) ?
    C1 C2 H2 . . 119.1 ?
    C3 C2 H2 . . 119.1 ?
    C4 C3 C2 . . 120.7(2) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C5 C4 C3 . . 118.2(2) ?
    C5 C4 C11 . . 120.3(2) ?
    C3 C4 C11 . . 121.5(2) ?
    C4 C5 C6 . . 121.0(2) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C5 C6 C1 . . 121.7(2) ?
    C5 C6 H6 . . 119.1 ?
    C1 C6 H6 . . 119.1 ?
    O1 C7 C8 . . 104.28(19) ?
    O1 C7 H7A . . 110.9 ?
    C8 C7 H7A . . 110.9 ?
    O1 C7 H7B . . 110.9 ?
    C8 C7 H7B . . 110.9 ?
    H7A C7 H7B . . 108.9 ?
    N1 C8 C7 . . 103.34(19) ?
    N1 C8 H8A . . 111.1 ?
    C7 C8 H8A . . 111.1 ?
    N1 C8 H8B . . 111.1 ?
    C7 C8 H8B . . 111.1 ?
    H8A C8 H8B . . 109.1 ?
    O2 C9 C10 . . 105.45(19) ?
    O2 C9 H9A . . 110.7 ?
    C10 C9 H9A . . 110.7 ?
    O2 C9 H9B . . 110.7 ?
    C10 C9 H9B . . 110.7 ?
    H9A C9 H9B . . 108.8 ?
    N1 C10 C9 . . 104.23(19) ?
    N1 C10 H10A . . 110.9 ?
    C9 C10 H10A . . 110.9 ?
    N1 C10 H10B . . 110.9 ?
    C9 C10 H10B . . 110.9 ?
    H10A C10 H10B . . 108.9 ?
    C12 C11 C4 . . 110.81(19) ?
    C12 C11 H11A . . 109.5 ?
    C4 C11 H11A . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    C4 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    O4 C12 O3 . . 123.2(3) ?
    O4 C12 C11 . . 124.8(3) ?
    O3 C12 C11 . . 112.0(2) ?
    O3 C13 H13A . . 109.5 ?
    O3 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    O3 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O1 B1 O2 . . 112.28(19) ?
    O1 B1 C1 . . 111.41(18) ?
    O2 B1 C1 . . 116.1(2) ?
    O1 B1 N1 . . 101.97(18) ?
    O2 B1 N1 . . 100.39(17) ?
    C1 B1 N1 . . 113.35(18) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    N1 H1 O2 . . 3_745 0.93 2.056 2.921(2) 154 y
    C10 H10B Cg3 . . 3_755 0.99 2.650 3.618(2) 166 y
data_global
_journal_date_recd_electronic     2010-09-07
_journal_date_accepted     2010-09-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     10
_journal_page_first     o2646
_journal_page_last     o2646
_journal_paper_category     QO
_journal_coeditor_code     FJ2337
_publ_contact_author_name     'Prof. P.E. Georghiou'
_publ_contact_author_address
;
Department of Chemistry
Memorial University of Newfoundland
St. Johns, NL, A1B 3X7
;
_publ_contact_author_email     'parisg@mun.ca'
_publ_contact_author_fax     '(709) 864-3702'
_publ_contact_author_phone     '(709) 864-8517'
_publ_section_title
;\
[2,2'-Iminodiethanolato(2-)-\k^3^<i>O</i>,<i>N</i>,<i>O</i>'][4-\
(methoxycarbonylmethyl)phenyl]boron
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zein, Ahmed L.' .
;
Department of Chemistry
Memorial University of Newfoundland
St Johns, NL, Canada A1B 3X7
;
    'Dawe, Louise N.' .
;
Department of Chemistry
Memorial University of Newfoundland
St Johns, NL, Canada A1B 3X7
;
    'Georghiou, Paris E.' .
;
Department of Chemistry
Memorial University of Newfoundland
St Johns, NL, Canada A1B 3X7
;
_cell_special_details     ?