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#$Date: 2023-02-02 11:19:17 +0200 (Thu, 02 Feb 2023) $
#$Revision: 280756 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106666.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_8106666
loop_
_publ_author_name
'Bai, JinYuan'
'Hou, YanJun'
_publ_section_title
;
 The crystal structure of
 [6-methoxy-2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1(2H)-one]difluoroborane,
 C13H10BF5O3
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              755
_journal_page_last               756
_journal_paper_doi               10.1515/ncrs-2017-0012
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C13 H10 B F5 O3'
_chemical_formula_sum            'C13 H10 B F5 O3'
_chemical_formula_weight         320.02
_chemical_name_systematic
; 
[6-methoxy-2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1(2H)
-one]difluoroborane
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                82.03(2)
_cell_angle_beta                 76.91(2)
_cell_angle_gamma                69.69(2)
_cell_formula_units_Z            2
_cell_length_a                   7.737(2)
_cell_length_b                   7.8600(19)
_cell_length_c                   11.803(3)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7252
_cell_measurement_theta_min      3.1837
_cell_volume                     654.2(3)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1954
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5444
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.791
_diffrn_reflns_theta_min         3.190
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0490P)²+0.1157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2390
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0012_suppl.cif
_cod_data_source_block           jyf-005
_cod_database_code               8106666
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.27975(16) 0.64622(17) 0.18252(10) 0.0447(3) Uani 1 1 d . . . . .
O2 O 1.27631(15) 0.66809(17) 0.38618(10) 0.0440(3) Uani 1 1 d . . . . .
F1 F 1.54142(15) 0.50139(17) 0.26436(10) 0.0632(3) Uani 1 1 d . . . . .
F2 F 1.44395(16) 0.80795(16) 0.23748(10) 0.0627(3) Uani 1 1 d . . . . .
F3 F 1.13462(17) 0.6912(2) 0.00592(9) 0.0780(4) Uani 1 1 d . . . . .
C7 C 1.0947(2) 0.7234(2) 0.40694(13) 0.0333(3) Uani 1 1 d . . . . .
C6 C 0.9995(2) 0.7440(2) 0.52610(13) 0.0350(3) Uani 1 1 d . . . . .
C8 C 0.9934(2) 0.7570(2) 0.31505(13) 0.0344(3) Uani 1 1 d . . . . .
F4 F 0.89597(18) 0.89960(17) 0.08623(10) 0.0687(4) Uani 1 1 d . . . . .
F5 F 0.90317(18) 0.62390(17) 0.11558(10) 0.0680(4) Uani 1 1 d . . . . .
O1 O 0.7459(2) 0.7796(2) 0.87210(11) 0.0624(4) Uani 1 1 d . . . . .
C4 C 0.7181(2) 0.7771(2) 0.67251(14) 0.0412(4) Uani 1 1 d . . . . .
H4 H 0.5910 0.7900 0.6933 0.049 Uiso 1 1 calc R U . . .
C11 C 1.0965(2) 0.7117(2) 0.20787(13) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.8070(2) 0.7643(2) 0.55668(13) 0.0350(3) Uani 1 1 d . . . . .
C1 C 1.0988(2) 0.7362(2) 0.61380(14) 0.0425(4) Uani 1 1 d . . . . .
H1 H 1.2264 0.7207 0.5942 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7042(2) 0.7612(2) 0.46317(14) 0.0395(4) Uani 1 1 d . . . . .
H10A H 0.5724 0.8307 0.4860 0.047 Uiso 1 1 calc R U . . .
H10B H 0.7134 0.6368 0.4559 0.047 Uiso 1 1 calc R U . . .
C3 C 0.8187(3) 0.7707(2) 0.75780(14) 0.0451(4) Uani 1 1 d . . . . .
C9 C 0.7827(2) 0.8397(2) 0.34558(14) 0.0414(4) Uani 1 1 d . . . . .
H9A H 0.7273 0.8167 0.2858 0.050 Uiso 1 1 calc R U . . .
H9B H 0.7490 0.9703 0.3478 0.050 Uiso 1 1 calc R U . . .
C12 C 1.0076(3) 0.7301(3) 0.10214(14) 0.0464(4) Uani 1 1 d . . . . .
C2 C 1.0094(3) 0.7511(3) 0.72725(15) 0.0485(4) Uani 1 1 d . . . . .
H2 H 1.0756 0.7482 0.7845 0.058 Uiso 1 1 calc R U . . .
B1 B 1.3926(3) 0.6553(3) 0.26566(17) 0.0423(4) Uani 1 1 d . . . . .
C13 C 0.5527(3) 0.7938(3) 0.91341(17) 0.0670(6) Uani 1 1 d . . . . .
H13A H 0.4742 0.9037 0.8798 0.101 Uiso 1 1 calc R U . . .
H13B H 0.5236 0.7962 0.9968 0.101 Uiso 1 1 calc R U . . .
H13C H 0.5308 0.6911 0.8913 0.101 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 O3 B1 120.14(13) . .
C7 O2 B1 123.13(13) . .
O2 C7 C8 121.05(14) . .
O2 C7 C6 117.66(13) . .
C8 C7 C6 121.26(14) . .
C1 C6 C5 119.44(15) . .
C1 C6 C7 120.48(14) . .
C5 C6 C7 120.02(13) . .
C11 C8 C7 116.47(14) . .
C11 C8 C9 126.22(14) . .
C7 C8 C9 117.31(14) . .
C3 O1 C13 119.85(16) . .
C5 C4 C3 120.01(16) . .
O3 C11 C8 125.19(14) . .
O3 C11 C12 112.23(14) . .
C8 C11 C12 122.58(14) . .
C4 C5 C6 119.58(14) . .
C4 C5 C10 121.20(14) . .
C6 C5 C10 119.13(14) . .
C2 C1 C6 120.48(16) . .
C5 C10 C9 112.21(13) . .
O1 C3 C4 124.43(17) . .
O1 C3 C2 115.25(16) . .
C4 C3 C2 120.31(15) . .
C8 C9 C10 111.30(13) . .
F3 C12 F5 108.41(15) . .
F3 C12 F4 107.28(15) . .
F5 C12 F4 107.02(15) . .
F3 C12 C11 111.92(15) . .
F5 C12 C11 111.77(14) . .
F4 C12 C11 110.21(14) . .
C1 C2 C3 120.17(16) . .
F1 B1 F2 112.68(15) . .
F1 B1 O3 109.15(15) . .
F2 B1 O3 109.15(15) . .
F1 B1 O2 108.06(15) . .
F2 B1 O2 108.32(15) . .
O3 B1 O2 109.42(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C11 1.3072(19) .
O3 B1 1.477(2) .
O2 C7 1.2936(18) .
O2 B1 1.497(2) .
F1 B1 1.349(2) .
F2 B1 1.367(2) .
F3 C12 1.316(2) .
C7 C8 1.422(2) .
C7 C6 1.435(2) .
C6 C1 1.405(2) .
C6 C5 1.408(2) .
C8 C11 1.354(2) .
C8 C9 1.507(2) .
F4 C12 1.327(2) .
F5 C12 1.322(2) .
O1 C3 1.340(2) .
O1 C13 1.433(2) .
C4 C5 1.384(2) .
C4 C3 1.391(2) .
C11 C12 1.524(2) .
C5 C10 1.507(2) .
C1 C2 1.361(2) .
C10 C9 1.522(2) .
C3 C2 1.395(3) .
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
_geom_hbond_site_symmetry_A
C9 H9A F4 0.97 2.54 3.005(2) 109.5 .
C9 H9A F5 0.97 2.52 3.186(2) 125.6 .
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
B1 O2 C7 C8 7.1(2) . . . .
B1 O2 C7 C6 -174.84(14) . . . .
O2 C7 C6 C1 11.2(2) . . . .
C8 C7 C6 C1 -170.74(14) . . . .
O2 C7 C6 C5 -166.01(14) . . . .
C8 C7 C6 C5 12.1(2) . . . .
O2 C7 C8 C11 6.1(2) . . . .
C6 C7 C8 C11 -171.96(13) . . . .
O2 C7 C8 C9 -173.71(14) . . . .
C6 C7 C8 C9 8.2(2) . . . .
B1 O3 C11 C8 -14.1(2) . . . .
B1 O3 C11 C12 166.71(14) . . . .
C7 C8 C11 O3 -2.4(2) . . . .
C9 C8 C11 O3 177.35(15) . . . .
C7 C8 C11 C12 176.65(14) . . . .
C9 C8 C11 C12 -3.6(3) . . . .
C3 C4 C5 C6 0.3(2) . . . .
C3 C4 C5 C10 176.83(15) . . . .
C1 C6 C5 C4 0.3(2) . . . .
C7 C6 C5 C4 177.50(14) . . . .
C1 C6 C5 C10 -176.32(14) . . . .
C7 C6 C5 C10 0.9(2) . . . .
C5 C6 C1 C2 -1.1(2) . . . .
C7 C6 C1 C2 -178.29(15) . . . .
C4 C5 C10 C9 151.40(15) . . . .
C6 C5 C10 C9 -32.0(2) . . . .
C13 O1 C3 C4 1.1(3) . . . .
C13 O1 C3 C2 -177.99(17) . . . .
C5 C4 C3 O1 -179.12(16) . . . .
C5 C4 C3 C2 -0.1(3) . . . .
C11 C8 C9 C10 141.33(16) . . . .
C7 C8 C9 C10 -38.9(2) . . . .
C5 C10 C9 C8 49.58(18) . . . .
O3 C11 C12 F3 -5.5(2) . . . .
C8 C11 C12 F3 175.28(15) . . . .
O3 C11 C12 F5 116.28(17) . . . .
C8 C11 C12 F5 -62.9(2) . . . .
O3 C11 C12 F4 -124.85(15) . . . .
C8 C11 C12 F4 56.0(2) . . . .
C6 C1 C2 C3 1.3(3) . . . .
O1 C3 C2 C1 178.41(16) . . . .
C4 C3 C2 C1 -0.7(3) . . . .
C11 O3 B1 F1 142.10(15) . . . .
C11 O3 B1 F2 -94.34(18) . . . .
C11 O3 B1 O2 24.0(2) . . . .
C7 O2 B1 F1 -139.80(15) . . . .
C7 O2 B1 F2 97.83(17) . . . .
C7 O2 B1 O3 -21.1(2) . . . .
