#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:06:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178691 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/02/4080257.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_4080257
loop_
_publ_author_name
'Dulong, Florian'
'Thuéry, Pierre'
'Ephritikhine, Michel'
'Cantat, Thibault'
_publ_section_title
;
 Synthesis ofN-Aryloxy-β-diketiminate Ligands and Coordination to
 Zirconium, Ytterbium, Thorium, and Uranium
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1328
_journal_paper_doi               10.1021/om3010355
_journal_volume                  32
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C19 H30 B F4 N O'
_chemical_formula_weight         375.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   10.5912(5)
_cell_length_b                   14.0519(7)
_cell_length_c                   14.0695(5)
_cell_measurement_reflns_used    35900
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.05
_cell_volume                     2093.91(16)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and one ω scans with 2° steps (238 frames)'
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            35900
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.026(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0932P)²+0.5343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                2014
_reflns_number_total             2253
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om3010355_si_002.cif
_cod_data_source_block           7
_cod_database_code               4080257
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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.0350(2) 1.12014(18) 0.84132(19) 0.0576(7) Uani 1 1 d .
N1 N 0.3627(3) 0.96071(18) 0.88536(18) 0.0438(6) Uani 1 1 d .
H1 H 0.4359 0.9887 0.9104 0.053 Uiso 1 1 d R
B1 B 0.6587(4) 1.0556(3) 0.9766(3) 0.0584(10) Uani 1 1 d .
F1 F 0.6130(2) 1.04157(19) 0.88567(17) 0.0768(7) Uani 1 1 d .
F2 F 0.5713(4) 1.0171(3) 1.0381(2) 0.1178(13) Uani 1 1 d .
F3 F 0.7744(3) 1.0122(2) 0.9841(2) 0.0886(9) Uani 1 1 d .
F4 F 0.6719(3) 1.15206(18) 0.9910(2) 0.0895(9) Uani 1 1 d .
C1 C 0.0408(3) 1.0283(3) 0.8193(2) 0.0550(8) Uani 1 1 d .
C2 C 0.1519(3) 0.9804(2) 0.8358(2) 0.0499(8) Uani 1 1 d .
H2 H 0.1515 0.9158 0.8216 0.060 Uiso 1 1 calc R
C3 C 0.2666(3) 1.0172(2) 0.8715(2) 0.0457(7) Uani 1 1 d .
C4 C -0.0709(4) 0.9801(4) 0.7797(4) 0.0766(12) Uani 1 1 d .
H4A H -0.1377 0.9806 0.8258 0.115 Uiso 1 1 calc R
H4B H -0.0497 0.9155 0.7642 0.115 Uiso 1 1 calc R
H4C H -0.0981 1.0127 0.7234 0.115 Uiso 1 1 calc R
C5 C 0.2885(3) 1.1208(2) 0.8932(3) 0.0528(8) Uani 1 1 d .
H5A H 0.3725 1.1292 0.9174 0.079 Uiso 1 1 calc R
H5B H 0.2285 1.1417 0.9399 0.079 Uiso 1 1 calc R
H5C H 0.2784 1.1575 0.8361 0.079 Uiso 1 1 calc R
C6 C -0.0809(4) 1.1748(3) 0.8242(3) 0.0694(11) Uani 1 1 d .
H6A H -0.0936 1.1841 0.7565 0.083 Uiso 1 1 calc R
H6B H -0.1535 1.1414 0.8497 0.083 Uiso 1 1 calc R
C7 C -0.0649(5) 1.2662(3) 0.8717(5) 0.1051(19) Uani 1 1 d .
H7A H -0.0513 1.2560 0.9384 0.158 Uiso 1 1 calc R
H7B H -0.1394 1.3041 0.8629 0.158 Uiso 1 1 calc R
H7C H 0.0066 1.2988 0.8452 0.158 Uiso 1 1 calc R
C8 C 0.3638(3) 0.8601(2) 0.8627(2) 0.0428(7) Uani 1 1 d .
C9 C 0.3168(3) 0.7951(3) 0.9294(2) 0.0505(8) Uani 1 1 d .
C10 C 0.3142(3) 0.7002(3) 0.9028(3) 0.0563(9) Uani 1 1 d .
H10 H 0.2832 0.6551 0.9451 0.068 Uiso 1 1 calc R
C11 C 0.3567(4) 0.6715(2) 0.8144(3) 0.0553(8) Uani 1 1 d .
H11 H 0.3528 0.6076 0.7977 0.066 Uiso 1 1 calc R
C12 C 0.4048(3) 0.7368(2) 0.7507(2) 0.0505(8) Uani 1 1 d .
H12 H 0.4335 0.7161 0.6917 0.061 Uiso 1 1 calc R
C13 C 0.4113(3) 0.8332(2) 0.7734(2) 0.0427(7) Uani 1 1 d .
C14 C 0.2739(4) 0.8270(3) 1.0273(3) 0.0635(10) Uani 1 1 d .
H14 H 0.2563 0.8954 1.0238 0.076 Uiso 1 1 calc R
C15 C 0.1559(6) 0.7789(7) 1.0609(5) 0.147(3) Uani 1 1 d U
H15A H 0.1700 0.7116 1.0649 0.220 Uiso 1 1 calc R
H15B H 0.0887 0.7913 1.0167 0.220 Uiso 1 1 calc R
H15C H 0.1332 0.8030 1.1224 0.220 Uiso 1 1 calc R
C16 C 0.3754(6) 0.8131(6) 1.1000(4) 0.118(2) Uani 1 1 d U
H16A H 0.3942 0.7465 1.1057 0.177 Uiso 1 1 calc R
H16B H 0.3471 0.8371 1.1602 0.177 Uiso 1 1 calc R
H16C H 0.4499 0.8468 1.0807 0.177 Uiso 1 1 calc R
C17 C 0.4709(4) 0.9039(2) 0.7053(2) 0.0505(8) Uani 1 1 d .
H17 H 0.4654 0.9669 0.7348 0.061 Uiso 1 1 calc R
C18 C 0.4009(5) 0.9085(4) 0.6116(3) 0.0877(15) Uani 1 1 d .
H18A H 0.4440 0.9511 0.5693 0.132 Uiso 1 1 calc R
H18B H 0.3165 0.9311 0.6223 0.132 Uiso 1 1 calc R
H18C H 0.3976 0.8462 0.5837 0.132 Uiso 1 1 calc R
C19 C 0.6097(4) 0.8817(3) 0.6909(3) 0.0721(12) Uani 1 1 d .
H19A H 0.6514 0.8799 0.7514 0.108 Uiso 1 1 calc R
H19B H 0.6473 0.9301 0.6520 0.108 Uiso 1 1 calc R
H19C H 0.6182 0.8210 0.6601 0.108 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
C1 O1 C6 120.6(3)
C3 N1 C8 124.5(3)
C3 N1 H1 116.5
C8 N1 H1 119.0
F3 B1 F4 109.6(4)
F3 B1 F2 112.2(4)
F4 B1 F2 111.3(4)
F3 B1 F1 108.7(4)
F4 B1 F1 108.2(3)
F2 B1 F1 106.8(3)
O1 C1 C2 118.4(3)
O1 C1 C4 119.8(4)
C2 C1 C4 121.8(4)
C1 C2 C3 128.1(3)
C1 C2 H2 115.9
C3 C2 H2 115.9
N1 C3 C2 120.1(3)
N1 C3 C5 116.0(3)
C2 C3 C5 123.9(3)
C1 C4 H4A 109.5
C1 C4 H4B 109.5
H4A C4 H4B 109.5
C1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 O1 106.8(4)
C7 C6 H6A 110.4
O1 C6 H6A 110.4
C7 C6 H6B 110.4
O1 C6 H6B 110.4
H6A C6 H6B 108.6
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 123.4(3)
C9 C8 N1 119.1(3)
C13 C8 N1 117.5(3)
C10 C9 C8 117.0(3)
C10 C9 C14 121.5(3)
C8 C9 C14 121.5(3)
C11 C10 C9 121.2(3)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 120.7(3)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 121.0(3)
C11 C12 H12 119.5
C13 C12 H12 119.5
C12 C13 C8 116.7(3)
C12 C13 C17 120.8(3)
C8 C13 C17 122.5(3)
C16 C14 C15 109.0(4)
C16 C14 C9 111.5(4)
C15 C14 C9 113.7(4)
C16 C14 H14 107.4
C15 C14 H14 107.4
C9 C14 H14 107.4
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C18 C17 C19 111.6(4)
C18 C17 C13 112.0(3)
C19 C17 C13 110.7(3)
C18 C17 H17 107.5
C19 C17 H17 107.5
C13 C17 H17 107.5
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.329(5)
O1 C6 1.468(5)
N1 C3 1.305(4)
N1 C8 1.450(4)
N1 H1 0.9382
B1 F3 1.372(5)
B1 F4 1.377(5)
B1 F2 1.378(6)
B1 F1 1.382(5)
C1 C2 1.375(5)
C1 C4 1.473(6)
C2 C3 1.413(5)
C2 H2 0.9300
C3 C5 1.505(5)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C7 1.458(7)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.400(5)
C8 C13 1.405(4)
C9 C10 1.385(5)
C9 C14 1.519(5)
C10 C11 1.383(6)
C10 H10 0.9300
C11 C12 1.380(5)
C11 H11 0.9300
C12 C13 1.393(4)
C12 H12 0.9300
C13 C17 1.518(4)
C14 C16 1.496(7)
C14 C15 1.497(7)
C14 H14 0.9800
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 C18 1.515(5)
C17 C19 1.516(6)
C17 H17 0.9800
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 F1 0.94 2.05 2.884(4) 147.7
N1 H1 F2 0.94 2.33 3.181(5) 150.4
