#------------------------------------------------------------------------------
#$Date: 2015-12-07 22:22:44 +0200 (Mon, 07 Dec 2015) $
#$Revision: 170874 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/75/7037574.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_7037574
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         'C13 H20 B N O2'
_chemical_formula_sum            'C13 H20 B N O2'
_chemical_formula_weight         233.11
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2014-06-26 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.41(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.416(4)
_cell_length_b                   9.961(2)
_cell_length_c                   13.900(3)
_cell_measurement_temperature    150
_cell_volume                     2549.1(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8224
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         4.092
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0575P)²+1.9006P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1498
_reflns_number_total             2322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt03835a2.cif
_cod_data_source_block           exp_474_refinalise
_cod_original_cell_volume        2549.0(9)
_cod_database_code               7037574
_shelxl_version_number           2013-2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C1(H1b,H1a), C4(H4b,H4a), C2(H2a,H2b), C3(H3a,H3b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9a), C12(H12a), C8(H8a), C13(H13a)
2.c Idealised Me refined as rotating group:
 C11(H11b,H11c,H11a)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.29178(10) 0.03313(17) 0.84396(12) 0.0218(5) Uani 1 1 d .
O O 0.21344(10) -0.05568(16) 0.71868(12) 0.0211(5) Uani 1 1 d .
N3 N 0.25580(13) 0.1824(2) 0.70345(16) 0.0215(6) Uani 1 1 d .
C4 C 0.16417(15) 0.1207(2) 0.84150(18) 0.0195(6) Uani 1 1 d .
B5 B 0.23027(18) 0.0620(3) 0.7792(2) 0.0193(7) Uani 1 1 d .
C6 C 0.11932(16) 0.2904(3) 0.95416(19) 0.0258(7) Uani 1 1 d .
H6 H 0.1285 0.3677 0.9900 0.031 Uiso 1 1 calc R
C7 C 0.16434(16) -0.0405(3) 0.63815(19) 0.0253(7) Uani 1 1 d .
H7A H 0.1164 -0.0194 0.6613 0.030 Uiso 1 1 calc R
H7B H 0.1610 -0.1251 0.6038 0.030 Uiso 1 1 calc R
C C 0.35991(15) 0.0092(3) 0.80149(19) 0.0243(7) Uani 1 1 d .
HA H 0.3559 -0.0675 0.7587 0.029 Uiso 1 1 calc R
HB H 0.3958 -0.0118 0.8515 0.029 Uiso 1 1 calc R
C9 C 0.04064(17) 0.1121(3) 0.9037(2) 0.0292(7) Uani 1 1 d .
H9 H -0.0039 0.0683 0.9053 0.035 Uiso 1 1 calc R
C10 C 0.20023(16) 0.2000(3) 0.62352(19) 0.0234(7) Uani 1 1 d .
H10A H 0.2168 0.2681 0.5793 0.028 Uiso 1 1 calc R
H10B H 0.1549 0.2304 0.6501 0.028 Uiso 1 1 calc R
C11 C 0.38499(16) 0.1313(3) 0.7449(2) 0.0267(7) Uani 1 1 d .
H11A H 0.3897 0.2081 0.7875 0.032 Uiso 1 1 calc R
H11B H 0.4321 0.1135 0.7180 0.032 Uiso 1 1 calc R
C12 C 0.17367(16) 0.2373(3) 0.89759(19) 0.0238(7) Uani 1 1 d .
H12 H 0.2183 0.2809 0.8968 0.029 Uiso 1 1 calc R
C13 C 0.05147(16) 0.2293(3) 0.95776(19) 0.0252(7) Uani 1 1 d .
C14 C 0.32996(15) 0.1620(3) 0.66430(19) 0.0253(7) Uani 1 1 d .
H14A H 0.3447 0.2424 0.6305 0.030 Uiso 1 1 calc R
H14B H 0.3287 0.0883 0.6187 0.030 Uiso 1 1 calc R
C15 C 0.18739(17) 0.0686(3) 0.56902(19) 0.0252(7) Uani 1 1 d .
H15A H 0.1499 0.0814 0.5197 0.030 Uiso 1 1 calc R
H15B H 0.2316 0.0417 0.5378 0.030 Uiso 1 1 calc R
C16 C 0.09553(16) 0.0600(3) 0.84758(19) 0.0263(7) Uani 1 1 d .
H16 H 0.0864 -0.0180 0.8127 0.032 Uiso 1 1 calc R
C17 C -0.00831(17) 0.2847(3) 1.0197(2) 0.0349(8) Uani 1 1 d .
H17A H -0.0191 0.2212 1.0693 0.052 Uiso 1 1 calc GR
H17B H -0.0511 0.3003 0.9804 0.052 Uiso 1 1 calc GR
H17C H 0.0075 0.3677 1.0485 0.052 Uiso 1 1 calc GR
H3 H 0.2611(15) 0.261(3) 0.734(2) 0.031(8) Uiso 1 1 d .
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C O1 B5 117.2(2)
C7 O B5 118.9(2)
C10 N3 B5 110.7(2)
C14 N3 B5 113.9(2)
C14 N3 C10 111.0(2)
C12 C4 B5 120.6(2)
C16 C4 B5 124.5(2)
C16 C4 C12 114.9(2)
O1 B5 O 110.2(2)
O1 B5 N3 107.7(2)
O1 B5 C4 108.9(2)
O B5 N3 105.7(2)
O B5 C4 116.3(2)
C4 B5 N3 107.8(2)
C13 C6 C12 120.8(3)
O C7 C15 112.9(2)
O1 C C11 111.2(2)
C16 C9 C13 121.0(3)
N3 C10 C15 111.1(2)
C14 C11 C 109.6(2)
C6 C12 C4 123.0(3)
C6 C13 C9 117.5(2)
C6 C13 C17 121.7(2)
C9 C13 C17 120.8(3)
N3 C14 C11 110.9(2)
C7 C15 C10 110.0(2)
C9 C16 C4 122.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 B5 1.458(4)
O1 C 1.420(3)
O B5 1.472(3)
O C7 1.429(3)
N3 B5 1.671(4)
N3 C10 1.502(3)
N3 C14 1.496(3)
C4 B5 1.620(4)
C4 C12 1.408(4)
C4 C16 1.405(4)
C6 C12 1.392(4)
C6 C13 1.392(4)
C7 C15 1.518(4)
C C11 1.526(4)
C9 C13 1.399(4)
C9 C16 1.392(4)
C10 C15 1.528(4)
C11 C14 1.523(4)
C13 C17 1.518(4)
