#------------------------------------------------------------------------------
#$Date: 2015-12-07 22:22:44 +0200 (Mon, 07 Dec 2015) $
#$Revision: 170874 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/75/7037573.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_7037573
loop_
_publ_author_name
'Dunsford, Jay J.'
'Clark, Ewan R.'
'Ingleson, Michael J.'
_publ_section_title
;
 Highly nucleophilic dipropanolamine chelated boron reagents for
 aryl-transmetallation to iron complexes.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              20577
_journal_page_last               20583
_journal_paper_doi               10.1039/c5dt03835a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C12 H18 B N O2, H2 O'
_chemical_formula_sum            'C12 H20 B N O3'
_chemical_formula_weight         237.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-06-26 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.84(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7171(19)
_cell_length_b                   11.890(2)
_cell_length_c                   11.565(2)
_cell_measurement_temperature    150
_cell_volume                     1222.2(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9888
_diffrn_measured_fraction_theta_max 0.9888
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4143
_diffrn_reflns_theta_full        25.3444
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2885
_exptl_crystal_description       block
_exptl_crystal_F_000             512.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4644
_refine_diff_density_min         -0.4517
_refine_diff_density_rms         0.1232
_refine_ls_d_res_high            0.8302
_refine_ls_d_res_low             4.9415
_refine_ls_goodness_of_fit_ref   1.0344
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0344
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0432P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -6
_reflns_number_gt                1288
_reflns_number_total             2206
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5dt03835a2.cif
_cod_data_source_block           amji117_refinalise2
_cod_database_code               7037573
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2(H2a,H2b)
2.b Ternary CH refined with riding coordinates:
 N4(H4)
2.c Secondary CH2 refined with riding coordinates:
 c5(H5a,H5b), c7(H7a,H7b), c8(H8a,H8b), c9(H9a,H9b), c10(H10a,H10b), c12(H12a,
 H12b)
2.d Aromatic/amide H refined with riding coordinates:
 c14(H14), c6(H6), c13(H13), c16(H16), c11(H11)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O1 O 0.17523(19) 0.62861(19) 0.16877(17) 0.0220(6) Uani 1.000000 .
O2 O 0.4910(2) 0.8048(2) 0.41899(19) 0.0318(6) Uani 1.000000 .
O3 O 0.2669(2) 0.63929(18) 0.39440(18) 0.0232(6) Uani 1.000000 .
N4 N 0.1733(2) 0.4564(2) 0.2927(2) 0.0219(7) Uani 1.000000 .
c5 C 0.2720(3) 0.4751(3) 0.5254(3) 0.0302(9) Uani 1.000000 .
c6 C -0.1913(3) 0.7566(3) 0.2955(3) 0.0331(9) Uani 1.000000 .
c7 C 0.1610(3) 0.4157(3) 0.4099(3) 0.0278(8) Uani 1.000000 .
c8 C 0.3350(3) 0.4699(3) 0.1739(3) 0.0266(8) Uani 1.000000 .
c9 C 0.3153(3) 0.5963(3) 0.1669(3) 0.0252(8) Uani 1.000000 .
c10 C 0.2611(3) 0.6023(3) 0.5103(3) 0.0274(9) Uani 1.000000 .
c11 C -0.1455(3) 0.5721(3) 0.1715(3) 0.0277(9) Uani 1.000000 .
c12 C 0.3201(3) 0.4227(3) 0.2898(3) 0.0267(8) Uani 1.000000 .
c13 C -0.3134(3) 0.7009(3) 0.2084(3) 0.0354(10) Uani 1.000000 .
c14 C -0.0468(3) 0.7208(3) 0.3188(3) 0.0273(8) Uani 1.000000 .
c15 C -0.0192(3) 0.6271(3) 0.2574(3) 0.0223(8) Uani 1.000000 .
c16 C -0.2916(3) 0.6078(3) 0.1467(3) 0.0332(9) Uani 1.000000 .
B17 B 0.1505(4) 0.5939(3) 0.2793(3) 0.0215(9) Uani 1.000000 .
H14 H 0.0345(3) 0.7601(3) 0.3770(3) 0.0328(10) Uiso 1.000000 R
H6 H -0.2058(3) 0.8183(3) 0.3387(3) 0.0397(11) Uiso 1.000000 R
H13 H -0.4104(3) 0.7260(3) 0.1913(3) 0.0425(12) Uiso 1.000000 R
H16 H -0.3738(3) 0.5691(3) 0.0889(3) 0.0398(11) Uiso 1.000000 R
H11 H -0.1322(3) 0.5093(3) 0.1291(3) 0.0333(10) Uiso 1.000000 R
H4 H 0.0982(2) 0.4239(2) 0.2254(2) 0.0262(8) Uiso 1.000000 R
H5a H 0.2529(3) 0.4539(3) 0.5986(3) 0.0363(11) Uiso 1.000000 R
H5b H 0.3732(3) 0.4512(3) 0.5402(3) 0.0363(11) Uiso 1.000000 R
H7a H 0.0596(3) 0.4288(3) 0.4036(3) 0.0334(10) Uiso 1.000000 R
H7b H 0.1798(3) 0.3354(3) 0.4185(3) 0.0334(10) Uiso 1.000000 R
H8a H 0.2597(3) 0.4359(3) 0.0986(3) 0.0320(10) Uiso 1.000000 R
H8b H 0.4334(3) 0.4511(3) 0.1766(3) 0.0320(10) Uiso 1.000000 R
H9a H 0.3207(3) 0.6238(3) 0.0899(3) 0.0303(10) Uiso 1.000000 R
H9b H 0.3966(3) 0.6306(3) 0.2380(3) 0.0303(10) Uiso 1.000000 R
H10a H 0.3432(3) 0.6367(3) 0.5808(3) 0.0329(10) Uiso 1.000000 R
H10b H 0.1675(3) 0.6276(3) 0.5130(3) 0.0329(10) Uiso 1.000000 R
H12a H 0.4021(3) 0.4502(3) 0.3652(3) 0.0321(10) Uiso 1.000000 R
H12b H 0.3267(3) 0.3413(3) 0.2892(3) 0.0321(10) Uiso 1.000000 R
H2a H 0.541(3) 0.823(3) 0.4957(9) 0.0477(10) Uiso 1.000000 G
H2b H 0.421(2) 0.760(2) 0.415(2) 0.0477(10) Uiso 1.000000 G
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
B17 O1 c9 115.9(2)
B17 O3 c10 115.5(2)
c12 N4 c7 111.2(2)
B17 N4 c7 110.5(3)
B17 N4 c12 110.9(2)
c10 c5 c7 111.8(3)
c14 c6 c13 120.1(3)
c5 c7 N4 111.2(3)
c12 c8 c9 111.1(3)
c8 c9 O1 111.6(3)
c5 c10 O3 112.6(3)
c16 c11 c15 122.3(3)
c8 c12 N4 110.8(2)
c16 c13 c6 119.8(3)
c15 c14 c6 122.0(3)
c14 c15 c11 116.2(3)
B17 c15 c11 123.2(3)
B17 c15 c14 120.5(3)
c13 c16 c11 119.6(3)
O3 B17 O1 110.8(3)
N4 B17 O1 107.5(3)
N4 B17 O3 104.8(2)
c15 B17 O1 108.3(2)
c15 B17 O3 114.8(3)
c15 B17 N4 110.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 c9 1.423(3)
O1 B17 1.453(4)
O3 c10 1.434(3)
O3 B17 1.458(4)
N4 c7 1.489(4)
N4 c12 1.495(4)
N4 B17 1.649(5)
c5 c7 1.511(4)
c5 c10 1.522(5)
c6 c13 1.376(5)
c6 c14 1.385(4)
c8 c9 1.513(5)
c8 c12 1.513(4)
c11 c15 1.391(4)
c11 c16 1.396(4)
c13 c16 1.379(5)
c14 c15 1.404(4)
c15 B17 1.613(4)
