#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:28:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180507 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/76/7217638.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_7217638
loop_
_publ_author_name
'Liu, Xu'
'Zhang, Qian'
'Xin, Xiaoqing'
'Zhang, Rui'
'Zhang, Ning'
'Liang, Yongjiu'
'Dong, Dewen'
_publ_section_title
;
 BF3•Et2O-Mediated Intramolecular Cyclization of Unsaturated
 Amides: Convenient Synthesis of Dihydroquinolin-2-one-BF2 Complexes
;
_journal_issue                   68
_journal_name_full               'RSC Advances'
_journal_page_first              36234
_journal_page_last               36240
_journal_paper_doi               10.1039/C4RA06151A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C45 H38 B2 Cl2 F4 N2 O6'
_chemical_formula_weight         871.29
_chemical_melting_point          153(2)
_chemical_name_common
8-(2-Chlorophenyl)-2,2-difluoro-7-(4-methoxyphenyl)-4-methyl-7,8-dihydro-2H-[1,3,2]dioxaborinino[4,5-b]pyridin-1-ium-2-uide
_chemical_name_systematic        ?
_space_group_IT_number           2
_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                101.954(5)
_cell_angle_beta                 104.028(5)
_cell_angle_gamma                98.284(5)
_cell_formula_units_Z            1
_cell_length_a                   7.643(5)
_cell_length_b                   12.269(5)
_cell_length_c                   12.840(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1118.6(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.975
_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  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6123
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.210
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0884
_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)+(0.1848P)²+0.6504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2757
_refine_ls_wR_factor_ref         0.2992
_reflns_number_gt                3256
_reflns_number_total             4318
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ra06151a2.cif
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '151-155' was changed to '153(2)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7217638
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
C1 C 0.2789(7) -0.0017(5) 0.1248(4) 0.0864(14) Uani 1 1 d .
H1A H 0.2709 -0.0781 0.1329 0.130 Uiso 1 1 calc R
H1B H 0.1866 0.0310 0.1519 0.130 Uiso 1 1 calc R
H1C H 0.3987 0.0429 0.1666 0.130 Uiso 1 1 calc R
C2 C 0.2483(5) -0.0028(4) 0.0045(3) 0.0656(10) Uani 1 1 d .
C3 C 0.2502(5) 0.0922(3) -0.0350(3) 0.0549(8) Uani 1 1 d .
C4 C 0.2274(5) 0.0776(3) -0.1516(3) 0.0525(8) Uani 1 1 d .
C5 C 0.2719(6) 0.2069(4) 0.0299(3) 0.0648(10) Uani 1 1 d .
H5 H 0.2745 0.2191 0.1043 0.078 Uiso 1 1 calc R
C6 C 0.2882(6) 0.2949(3) -0.0138(3) 0.0672(10) Uani 1 1 d .
H6 H 0.2967 0.3665 0.0311 0.081 Uiso 1 1 calc R
C7 C 0.2936(5) 0.2873(3) -0.1299(3) 0.0563(8) Uani 1 1 d .
C8 C 0.2177(5) 0.1459(3) -0.3154(3) 0.0582(9) Uani 1 1 d .
C9 C 0.0564(5) 0.1566(3) -0.3853(3) 0.0618(9) Uani 1 1 d .
C10 C 0.0404(7) 0.1443(3) -0.4973(3) 0.0728(11) Uani 1 1 d .
H10 H -0.0679 0.1526 -0.5440 0.087 Uiso 1 1 calc R
C11 C 0.1812(7) 0.1201(4) -0.5394(4) 0.0768(12) Uani 1 1 d .
H11 H 0.1685 0.1103 -0.6148 0.092 Uiso 1 1 calc R
C12 C 0.3447(7) 0.1102(4) -0.4685(4) 0.0772(12) Uani 1 1 d .
H12 H 0.4412 0.0971 -0.4985 0.093 Uiso 1 1 calc R
C13 C 0.3722(5) 0.1186(3) -0.3577(3) 0.0617(9) Uani 1 1 d .
H13 H 0.4803 0.1079 -0.3127 0.074 Uiso 1 1 calc R
C14 C 0.4810(5) 0.3382(3) -0.1375(3) 0.0501(8) Uani 1 1 d .
C15 C 0.4984(6) 0.4058(3) -0.2096(3) 0.0612(9) Uani 1 1 d .
H15 H 0.3929 0.4222 -0.2519 0.073 Uiso 1 1 calc R
C16 C 0.6674(6) 0.4496(3) -0.2207(3) 0.0651(10) Uani 1 1 d .
H16 H 0.6757 0.4943 -0.2703 0.078 Uiso 1 1 calc R
C17 C 0.6409(5) 0.3153(3) -0.0746(3) 0.0573(9) Uani 1 1 d .
H17 H 0.6324 0.2705 -0.0251 0.069 Uiso 1 1 calc R
C18 C 0.8101(5) 0.3574(3) -0.0844(3) 0.0641(9) Uani 1 1 d .
H18 H 0.9152 0.3401 -0.0427 0.077 Uiso 1 1 calc R
C19 C 0.8250(5) 0.4262(3) -0.1568(3) 0.0591(9) Uani 1 1 d .
C20 C 1.0262(9) 0.5445(5) -0.2230(6) 0.1069(19) Uani 1 1 d .
H20A H 1.1546 0.5645 -0.2182 0.160 Uiso 1 1 calc R
H20B H 0.9840 0.6116 -0.1950 0.160 Uiso 1 1 calc R
H20C H 0.9571 0.5113 -0.2991 0.160 Uiso 1 1 calc R
C21 C 0.325(3) 0.5845(17) 0.5696(13) 0.119(5) Uani 0.50 1 d P
C22 C 0.450(5) 0.535(3) 0.5224(17) 0.189(13) Uani 0.50 1 d P
C23 C 0.615(2) 0.5808(12) 0.5287(12) 0.083(4) Uani 0.50 1 d P
C24 C 0.699(4) 0.543(4) 0.494(3) 0.24(2) Uani 0.50 1 d P
C25 C 0.496(5) 0.6372(15) 0.5809(16) 0.180(12) Uani 0.50 1 d P
B1 B 0.1735(7) -0.1288(4) -0.1792(4) 0.0691(12) Uani 1 1 d .
N1 N 0.2381(4) 0.1652(2) -0.1966(2) 0.0530(7) Uani 1 1 d .
O1 O 0.1954(4) -0.0222(2) -0.2182(2) 0.0667(7) Uani 1 1 d .
O2 O 0.2240(5) -0.1058(3) -0.0601(3) 0.0826(9) Uani 1 1 d .
O3 O 1.0009(4) 0.4652(2) -0.1594(3) 0.0767(8) Uani 1 1 d .
F1 F 0.2809(5) -0.1941(3) -0.2189(3) 0.1118(11) Uani 1 1 d .
F2 F -0.0100(4) -0.1815(2) -0.2210(2) 0.0968(9) Uani 1 1 d .
Cl1 Cl -0.12428(15) 0.18465(12) -0.33274(10) 0.0877(5) 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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O2 C2 C3 122.7(3) . .
O2 C2 C1 113.0(4) . .
C3 C2 C1 124.2(4) . .
C2 C3 C4 117.5(3) . .
C2 C3 C5 125.9(3) . .
C4 C3 C5 116.6(3) . .
O1 C4 N1 116.5(3) . .
O1 C4 C3 121.5(3) . .
N1 C4 C3 122.0(3) . .
C6 C5 C3 121.5(3) . .
C6 C5 H5 119.2 . .
C3 C5 H5 119.2 . .
C5 C6 C7 124.5(3) . .
C5 C6 H6 117.8 . .
C7 C6 H6 117.8 . .
C6 C7 N1 110.4(3) . .
C6 C7 C14 112.8(3) . .
N1 C7 C14 109.1(3) . .
C9 C8 N1 119.8(3) . .
C9 C8 C13 121.1(3) . .
N1 C8 C13 119.1(3) . .
C8 C9 C10 119.8(4) . .
C8 C9 Cl1 119.6(3) . .
C10 C9 Cl1 120.5(3) . .
C11 C10 C9 120.7(4) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C10 C11 C12 119.4(4) . .
C10 C11 H11 120.3 . .
C12 C11 H11 120.3 . .
C13 C12 C11 124.1(4) . .
C13 C12 H12 117.9 . .
C11 C12 H12 117.9 . .
C12 C13 C8 114.7(4) . .
C12 C13 H13 122.7 . .
C8 C13 H13 122.7 . .
C15 C14 C17 118.0(3) . .
C15 C14 C7 121.0(3) . .
C17 C14 C7 121.0(3) . .
C16 C15 C14 122.0(3) . .
C16 C15 H15 119.0 . .
C14 C15 H15 119.0 . .
C15 C16 C19 119.0(3) . .
C15 C16 H16 120.5 . .
C19 C16 H16 120.5 . .
C18 C17 C14 121.2(3) . .
C18 C17 H17 119.4 . .
C14 C17 H17 119.4 . .
C17 C18 C19 120.0(3) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
O3 C19 C16 124.7(3) . .
O3 C19 C18 115.4(3) . .
C16 C19 C18 119.8(4) . .
O3 C20 H20A 109.5 . .
O3 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O3 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C25 C21 C22 56(2) . .
C25 C21 C24 107.8(19) . 2_666
C22 C21 C24 53(2) . 2_666
C25 C22 C23 68(3) . .
C25 C22 C24 130(3) . 2_666
C23 C22 C24 161(3) . 2_666
C25 C22 C22 132(6) . 2_666
C23 C22 C22 64(3) . 2_666
C24 C22 C22 97(4) 2_666 2_666
C25 C22 C21 59.6(18) . .
C23 C22 C21 128(3) . .
C24 C22 C21 71(3) 2_666 .
C22 C22 C21 167(5) 2_666 .
C25 C22 C23 170(3) . 2_666
C23 C22 C23 119.1(15) . 2_666
C24 C22 C23 42(3) 2_666 2_666
C22 C22 C23 55(3) 2_666 2_666
C21 C22 C23 113(3) . 2_666
C25 C22 C24 92(3) . .
C23 C22 C24 23.5(17) . .
C24 C22 C24 138(2) 2_666 .
C22 C22 C24 41(3) 2_666 .
C21 C22 C24 151(3) . .
C23 C22 C24 95.7(16) 2_666 .
C24 C23 C22 125(3) . .
C24 C23 C22 65(2) . 2_666
C22 C23 C22 60.9(15) . 2_666
C24 C23 C25 179(3) . .
C22 C23 C25 55.7(16) . .
C22 C23 C25 116(2) 2_666 .
C23 C24 C22 73(2) . 2_666
C23 C24 C21 130(3) . 2_666
C22 C24 C21 56.9(18) 2_666 2_666
C23 C24 C22 31.1(15) . .
C22 C24 C22 42(2) 2_666 .
C21 C24 C22 98.8(18) 2_666 .
C22 C25 C21 64.8(19) . .
C22 C25 C23 56(2) . .
C21 C25 C23 120.9(17) . .
F1 B1 F2 111.2(4) . .
F1 B1 O2 109.7(4) . .
F2 B1 O2 109.0(4) . .
F1 B1 O1 107.9(4) . .
F2 B1 O1 107.0(4) . .
O2 B1 O1 112.2(3) . .
C4 N1 C8 119.8(3) . .
C4 N1 C7 123.4(3) . .
C8 N1 C7 116.4(3) . .
C4 O1 B1 122.1(3) . .
C2 O2 B1 122.6(3) . .
C19 O3 C20 117.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.502(6) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 O2 1.320(5) .
C2 C3 1.365(5) .
C3 C4 1.434(5) .
C3 C5 1.443(5) .
C4 O1 1.293(4) .
C4 N1 1.323(4) .
C5 C6 1.319(6) .
C5 H5 0.9300 .
C6 C7 1.486(6) .
C6 H6 0.9300 .
C7 N1 1.505(4) .
C7 C14 1.512(5) .
C8 C9 1.380(5) .
C8 N1 1.459(5) .
C8 C13 1.467(6) .
C9 C10 1.387(6) .
C9 Cl1 1.724(4) .
C10 C11 1.359(7) .
C10 H10 0.9300 .
C11 C12 1.394(7) .
C11 H11 0.9300 .
C12 C13 1.367(6) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C15 1.382(5) .
C14 C17 1.392(5) .
C15 C16 1.378(6) .
C15 H15 0.9300 .
C16 C19 1.388(6) .
C16 H16 0.9300 .
C17 C18 1.367(5) .
C17 H17 0.9300 .
C18 C19 1.392(6) .
C18 H18 0.9300 .
C19 O3 1.372(5) .
C20 O3 1.415(6) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C25 1.33(3) .
C21 C22 1.39(2) .
C21 C24 1.57(5) 2_666
C22 C25 1.27(3) .
C22 C23 1.28(4) .
C22 C24 1.32(5) 2_666
C22 C22 1.36(3) 2_666
C22 C23 1.40(4) 2_666
C22 C24 2.01(5) .
C23 C24 0.98(5) .
C23 C22 1.40(4) 2_666
C23 C25 1.43(4) .
C24 C22 1.32(5) 2_666
C24 C21 1.57(5) 2_666
B1 F1 1.341(6) .
B1 F2 1.380(6) .
B1 O2 1.439(6) .
B1 O1 1.496(5) .
