#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/41/7004124.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_7004124
loop_
_publ_author_name
'Ly, Hanh V.'
'Konu, Jari'
'Parvez, Masood'
'Roesler, Roland'
_publ_section_title
;
 Tuning the electronic properties of cyclopentadienyl analogs with
 CB2N2 frameworks: 1,2-diphenyl-1,2-diaza-3,5-diborolyl ligands and
 their alkali metal salts
;
_journal_issue                   26
_journal_name_full               'Dalton Transactions'
_journal_page_first              3454
_journal_page_last               3460
_journal_paper_doi               10.1039/b802930j
_journal_year                    2008
_chemical_formula_moiety         'C18 H26 B2 N4'
_chemical_formula_sum            'C18 H26 B2 N4'
_chemical_formula_weight         320.05
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.055(15)
_cell_angle_beta                 90.450(18)
_cell_angle_gamma                101.589(17)
_cell_formula_units_Z            2
_cell_length_a                   9.751(3)
_cell_length_b                   10.426(3)
_cell_length_c                   10.457(3)
_cell_measurement_reflns_used    6410
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      3.82
_cell_volume                     921.4(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        DENZO-SMN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'KappaCCD (Nonius, FR540C)'
_diffrn_measurement_method       'phiω scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Enraf Nonius FR590D, fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6410
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         3.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9905
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2618
_reflns_number_total             3333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802930j.txt
_cod_data_source_block           2
_cod_database_code               7004124
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.69334(13) 0.16261(14) 0.38178(13) 0.0237(3) Uani 1 1 d . . .
N2 N 0.68559(13) 0.23312(14) 0.29025(13) 0.0232(3) Uani 1 1 d . . .
N3 N 0.81874(13) -0.04083(14) 0.33856(14) 0.0264(3) Uani 1 1 d . . .
N4 N 0.86532(13) 0.37546(14) 0.20128(14) 0.0286(3) Uani 1 1 d . . .
C1 C 0.92755(15) 0.18687(16) 0.28825(16) 0.0240(3) Uani 1 1 d . . .
H1 H 0.9700 0.1270 0.2060 0.029 Uiso 1 1 d R . .
C2 C 1.04361(17) 0.29674(18) 0.41376(18) 0.0331(4) Uani 1 1 d . . .
H2A H 1.1098 0.3528 0.3800 0.040 Uiso 1 1 d R . .
H2B H 1.0915 0.2427 0.4457 0.040 Uiso 1 1 d R . .
H2C H 1.0019 0.3627 0.4927 0.040 Uiso 1 1 d R . .
C3 C 0.67579(15) 0.25043(17) 0.52809(16) 0.0248(3) Uani 1 1 d . . .
C4 C 0.70631(17) 0.20734(19) 0.63221(17) 0.0307(4) Uani 1 1 d . . .
H4 H 0.7436 0.1210 0.6041 0.037 Uiso 1 1 d R . .
C5 C 0.68479(18) 0.2897(2) 0.77481(18) 0.0365(4) Uani 1 1 d . . .
H5 H 0.7039 0.2583 0.8450 0.044 Uiso 1 1 d R . .
C6 C 0.63470(18) 0.4168(2) 0.81854(18) 0.0389(4) Uani 1 1 d . . .
H6 H 0.6199 0.4730 0.9176 0.047 Uiso 1 1 d R . .
C7 C 0.60653(18) 0.4610(2) 0.71684(18) 0.0366(4) Uani 1 1 d . . .
H7 H 0.5727 0.5495 0.7457 0.044 Uiso 1 1 d R . .
C8 C 0.62595(16) 0.37915(17) 0.57294(17) 0.0295(4) Uani 1 1 d . . .
H8 H 0.6061 0.4117 0.5038 0.035 Uiso 1 1 d R . .
C9 C 0.55273(15) 0.19324(16) 0.21150(15) 0.0227(3) Uani 1 1 d . . .
C10 C 0.42952(16) 0.14683(18) 0.26058(17) 0.0302(4) Uani 1 1 d . . .
H10 H 0.4346 0.1399 0.3489 0.036 Uiso 1 1 d R . .
C11 C 0.29995(18) 0.1088(2) 0.18094(19) 0.0382(4) Uani 1 1 d . . .
H11 H 0.2148 0.0780 0.2150 0.046 Uiso 1 1 d R . .
C12 C 0.28971(18) 0.11605(19) 0.05262(19) 0.0372(4) Uani 1 1 d . . .
H12 H 0.1986 0.0909 0.0008 0.045 Uiso 1 1 d R . .
C13 C 0.41155(18) 0.15900(18) 0.00223(17) 0.0331(4) Uani 1 1 d . . .
H13 H 0.4063 0.1626 -0.0878 0.040 Uiso 1 1 d R . .
C14 C 0.54173(17) 0.19630(16) 0.07955(16) 0.0264(4) Uani 1 1 d . . .
H14 H 0.6251 0.2248 0.0416 0.032 Uiso 1 1 d R . .
C15 C 0.70114(17) -0.13376(19) 0.36537(19) 0.0346(4) Uani 1 1 d . . .
H15A H 0.6248 -0.0845 0.3913 0.041 Uiso 1 1 d R . .
H15B H 0.7316 -0.1499 0.4433 0.041 Uiso 1 1 d R . .
H15C H 0.6701 -0.2271 0.2802 0.041 Uiso 1 1 d R . .
C16 C 0.93936(18) -0.10834(19) 0.2980(2) 0.0371(4) Uani 1 1 d . . .
H16A H 1.0127 -0.0434 0.2807 0.045 Uiso 1 1 d R . .
H16B H 0.9118 -0.2014 0.2118 0.045 Uiso 1 1 d R . .
H16C H 0.9733 -0.1241 0.3749 0.045 Uiso 1 1 d R . .
C17 C 0.78582(19) 0.48410(18) 0.21424(19) 0.0348(4) Uani 1 1 d . . .
H17A H 0.6975 0.4645 0.2495 0.042 Uiso 1 1 d R . .
H17B H 0.7687 0.4785 0.1211 0.042 Uiso 1 1 d R . .
H17C H 0.8393 0.5813 0.2803 0.042 Uiso 1 1 d R . .
C18 C 1.00043(19) 0.3990(2) 0.1476(2) 0.0426(5) Uani 1 1 d . . .
H18A H 1.0487 0.3248 0.1411 0.051 Uiso 1 1 d R . .
H18B H 1.0563 0.4952 0.2130 0.051 Uiso 1 1 d R . .
H18C H 0.9857 0.3924 0.0538 0.051 Uiso 1 1 d R . .
B1 B 0.81582(18) 0.09153(19) 0.33796(18) 0.0234(4) Uani 1 1 d . . .
B2 B 0.82667(18) 0.27095(18) 0.25123(18) 0.0234(4) Uani 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 N2 114.43(12) . . ?
C3 N1 B1 122.49(12) . . ?
N2 N1 B1 104.46(11) . . ?
C9 N2 N1 114.45(11) . . ?
C9 N2 B2 129.60(12) . . ?
N1 N2 B2 109.05(11) . . ?
B1 N3 C16 121.82(13) . . ?
B1 N3 C15 125.27(13) . . ?
C16 N3 C15 112.68(13) . . ?
B2 N4 C17 124.51(14) . . ?
B2 N4 C18 122.46(14) . . ?
C17 N4 C18 112.57(13) . . ?
C2 C1 B1 111.18(13) . . ?
C2 C1 B2 111.33(13) . . ?
B1 C1 B2 98.87(12) . . ?
C2 C1 H1 109.8 . . ?
B1 C1 H1 112.6 . . ?
B2 C1 H1 112.7 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.8 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 C4 118.22(14) . . ?
C8 C3 N1 121.84(14) . . ?
C4 C3 N1 119.93(14) . . ?
C5 C4 C3 120.38(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 121.15(16) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 118.71(16) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.07(17) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 120.46(15) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.6 . . ?
C10 C9 C14 118.20(14) . . ?
C10 C9 N2 121.36(13) . . ?
C14 C9 N2 120.43(13) . . ?
C11 C10 C9 120.08(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 121.32(16) . . ?
C12 C11 H11 118.4 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 118.77(15) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.74(15) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C9 120.85(15) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 120.0 . . ?
N3 C15 H15A 109.3 . . ?
N3 C15 H15B 109.0 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 110.1 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.2 . . ?
N3 C16 H16B 109.7 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.6 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 H17A 109.9 . . ?
N4 C17 H17B 109.2 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.3 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 109.4 . . ?
N4 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.7 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 B1 N1 122.07(14) . . ?
N3 B1 C1 128.92(14) . . ?
N1 B1 C1 108.95(13) . . ?
N4 B2 N2 123.51(14) . . ?
N4 B2 C1 126.75(14) . . ?
N2 B2 C1 109.52(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.4146(19) . ?
N1 N2 1.4572(17) . ?
N1 B1 1.497(2) . ?
N2 C9 1.4087(19) . ?
N2 B2 1.467(2) . ?
N3 B1 1.389(2) . ?
N3 C16 1.459(2) . ?
N3 C15 1.462(2) . ?
N4 B2 1.399(2) . ?
N4 C17 1.455(2) . ?
N4 C18 1.455(2) . ?
C1 C2 1.550(2) . ?
C1 B1 1.578(2) . ?
C1 B2 1.592(2) . ?
C1 H1 0.9600 . ?
C2 H2A 0.9601 . ?
C2 H2B 0.9601 . ?
C2 H2C 0.9599 . ?
C3 C8 1.397(2) . ?
C3 C4 1.403(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.9599 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9601 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9600 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9600 . ?
C8 H8 0.9600 . ?
C9 C10 1.394(2) . ?
C9 C14 1.398(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9600 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9600 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9599 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9601 . ?
C14 H14 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9599 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9599 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9599 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C9 -97.20(14) . . . . ?
B1 N1 N2 C9 126.20(13) . . . . ?
C3 N1 N2 B2 108.94(14) . . . . ?
B1 N1 N2 B2 -27.66(15) . . . . ?
N2 N1 C3 C8 12.84(19) . . . . ?
B1 N1 C3 C8 140.76(15) . . . . ?
N2 N1 C3 C4 -168.36(13) . . . . ?
B1 N1 C3 C4 -40.4(2) . . . . ?
C8 C3 C4 C5 1.1(2) . . . . ?
N1 C3 C4 C5 -177.72(14) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C3 -0.6(2) . . . . ?
C4 C3 C8 C7 -0.4(2) . . . . ?
N1 C3 C8 C7 178.38(14) . . . . ?
N1 N2 C9 C10 26.38(19) . . . . ?
B2 N2 C9 C10 173.67(15) . . . . ?
N1 N2 C9 C14 -152.21(13) . . . . ?
B2 N2 C9 C14 -4.9(2) . . . . ?
C14 C9 C10 C11 -1.6(2) . . . . ?
N2 C9 C10 C11 179.73(14) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C9 -0.9(2) . . . . ?
C10 C9 C14 C13 2.1(2) . . . . ?
N2 C9 C14 C13 -179.23(14) . . . . ?
C16 N3 B1 N1 -178.98(14) . . . . ?
C15 N3 B1 N1 7.0(2) . . . . ?
C16 N3 B1 C1 4.0(2) . . . . ?
C15 N3 B1 C1 -170.02(15) . . . . ?
C3 N1 B1 N3 81.56(19) . . . . ?
N2 N1 B1 N3 -146.32(14) . . . . ?
C3 N1 B1 C1 -100.92(15) . . . . ?
N2 N1 B1 C1 31.19(15) . . . . ?
C2 C1 B1 N3 -87.22(19) . . . . ?
B2 C1 B1 N3 155.69(16) . . . . ?
C2 C1 B1 N1 95.48(15) . . . . ?
B2 C1 B1 N1 -21.60(15) . . . . ?
C17 N4 B2 N2 15.6(2) . . . . ?
C18 N4 B2 N2 -172.78(15) . . . . ?
C17 N4 B2 C1 -158.39(15) . . . . ?
C18 N4 B2 C1 13.2(2) . . . . ?
C9 N2 B2 N4 50.6(2) . . . . ?
N1 N2 B2 N4 -160.78(14) . . . . ?
C9 N2 B2 C1 -134.49(15) . . . . ?
N1 N2 B2 C1 14.14(16) . . . . ?
C2 C1 B2 N4 62.4(2) . . . . ?
B1 C1 B2 N4 179.39(15) . . . . ?
C2 C1 B2 N2 -112.28(14) . . . . ?
B1 C1 B2 N2 4.68(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652666
