#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:44:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180313 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/27/7152761.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_7152761
loop_
_publ_author_name
'Deponti, Monica'
'Kozhushkov, Sergei I.'
'Yufit, Dmitry S.'
'Ackermann, Lutz'
_publ_section_title
;
 Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations:
 oxidative annulations of cyclopropyl-substituted alkynes.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              142
_journal_page_last               148
_journal_paper_doi               10.1039/c2ob26250a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C19 H13 F3 O2'
_chemical_formula_sum            'C19 H13 F3 O2'
_chemical_formula_weight         330.29
_chemical_name_common
4-cyclopropyl-3-(3-trifluoromethylphenyl-1H-isochromen-1-one
_chemical_name_systematic
;
4-cyclopropyl-3-(3-trifluoromethylphenyl-1H-isochromen-1-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-04-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2012.03.20 svn.r2253, GUI svn.r4124)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.502(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3582(7)
_cell_length_b                   14.6219(8)
_cell_length_c                   7.6852(4)
_cell_measurement_reflns_used    7488
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.79
_cell_volume                     1501.03(14)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22487
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0455 before and 0.0249 after correction.
The Ratio of minimum to maximum transmission is 0.6522.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.990
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0754
_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)+(0.1000P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2099
_reflns_number_gt                3002
_reflns_number_total             3608
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26250a.txt
_cod_data_source_block           6ae_dk80
_cod_database_code               7152761
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.0837(3) 0.4517(2) 0.2372(7) 0.0452(12) Uiso 0.50 1 d PD A 1
F1A F -0.0986(4) 0.4431(3) 0.1823(9) 0.0232(11) Uiso 0.30 1 d PD A 2
F1B F -0.1176(11) 0.4138(11) 0.1185(17) 0.077(4) Uiso 0.20 1 d PD A 3
F2 F -0.1086(3) 0.3241(4) 0.3798(5) 0.0494(10) Uiso 0.50 1 d PD A 1
F2A F -0.0859(5) 0.3573(5) 0.4111(5) 0.0278(11) Uiso 0.30 1 d PD A 2
F2B F -0.0600(10) 0.3976(9) 0.3955(10) 0.062(3) Uiso 0.20 1 d PD A 3
F3 F -0.1420(3) 0.3324(3) 0.1112(6) 0.0542(11) Uiso 0.50 1 d PD A 1
F3A F -0.1490(4) 0.3042(5) 0.1822(11) 0.0492(16) Uiso 0.30 1 d PD A 2
F3B F -0.1321(7) 0.2907(5) 0.2921(15) 0.048(2) Uiso 0.20 1 d PD A 3
O1 O 0.31973(13) 0.38774(12) -0.1220(2) 0.0259(4) Uani 1 1 d . . .
O2 O 0.42603(15) 0.39324(13) -0.3387(2) 0.0320(5) Uani 1 1 d . . .
C1 C 0.38951(18) 0.43366(17) -0.2175(3) 0.0248(5) Uani 1 1 d . . .
C2 C 0.26927(17) 0.42681(17) 0.0167(3) 0.0235(5) Uani 1 1 d . . .
C3 C 0.28859(18) 0.51255(16) 0.0721(3) 0.0239(5) Uani 1 1 d . . .
C4 C 0.36100(18) 0.56683(16) -0.0234(3) 0.0231(5) Uani 1 1 d . . .
C5 C 0.3823(2) 0.65842(17) 0.0185(3) 0.0273(5) Uani 1 1 d . . .
C6 C 0.4528(2) 0.70680(18) -0.0743(3) 0.0296(5) Uani 1 1 d . . .
C7 C 0.5047(2) 0.66595(18) -0.2105(3) 0.0291(5) Uani 1 1 d . . .
C8 C 0.48319(19) 0.57705(18) -0.2575(3) 0.0270(5) Uani 1 1 d . . .
C9 C 0.41150(18) 0.52760(16) -0.1645(3) 0.0239(5) Uani 1 1 d . . .
C10 C 0.23844(19) 0.55211(17) 0.2281(3) 0.0274(5) Uani 1 1 d . . .
C11 C 0.3007(2) 0.5826(2) 0.3836(4) 0.0334(6) Uani 1 1 d . . .
C12 C 0.2359(2) 0.4992(2) 0.3964(4) 0.0353(6) Uani 1 1 d . . .
C13 C 0.19469(18) 0.36102(17) 0.0820(3) 0.0252(5) Uani 1 1 d . . .
C14 C 0.09903(19) 0.39045(18) 0.1290(3) 0.0269(5) Uani 1 1 d . . .
C15 C 0.02898(19) 0.32749(19) 0.1856(3) 0.0291(5) Uani 1 1 d . A .
C16 C 0.0514(2) 0.23491(19) 0.1957(3) 0.0304(6) Uani 1 1 d . . .
C17 C 0.1460(2) 0.20557(18) 0.1480(3) 0.0298(6) Uani 1 1 d . . .
C18 C 0.2171(2) 0.26773(17) 0.0914(3) 0.0269(5) Uani 1 1 d . . .
C19 C -0.0733(2) 0.35907(17) 0.2351(3) 0.0407(7) Uani 1 1 d D . .
H5 H 0.347(2) 0.687(2) 0.120(4) 0.034(8) Uiso 1 1 d . . .
H6 H 0.469(3) 0.769(3) -0.041(5) 0.044(10) Uiso 1 1 d . . .
H7 H 0.556(3) 0.700(2) -0.276(4) 0.033(8) Uiso 1 1 d . . .
H8 H 0.515(2) 0.548(2) -0.355(4) 0.022(7) Uiso 1 1 d . . .
H10 H 0.179(2) 0.589(2) 0.201(4) 0.029(8) Uiso 1 1 d . . .
H11A H 0.374(3) 0.573(2) 0.379(4) 0.032(8) Uiso 1 1 d . . .
H11B H 0.280(3) 0.639(3) 0.444(5) 0.044(10) Uiso 1 1 d . . .
H12A H 0.179(3) 0.503(3) 0.465(5) 0.049(10) Uiso 1 1 d . . .
H12B H 0.271(3) 0.437(3) 0.394(5) 0.043(9) Uiso 1 1 d . . .
H14 H 0.081(3) 0.453(3) 0.117(5) 0.039(9) Uiso 1 1 d . . .
H16 H 0.002(3) 0.191(3) 0.237(5) 0.038(9) Uiso 1 1 d . . .
H17 H 0.164(3) 0.140(3) 0.153(5) 0.038(9) Uiso 1 1 d . . .
H18 H 0.284(2) 0.248(2) 0.064(4) 0.027(7) 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'
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
C1 O1 C2 123.19(19)
O1 C1 C9 116.6(2)
O2 C1 O1 117.0(2)
O2 C1 C9 126.3(2)
O1 C2 C13 109.1(2)
C3 C2 O1 122.2(2)
C3 C2 C13 128.8(2)
C2 C3 C4 118.3(2)
C2 C3 C10 121.8(2)
C4 C3 C10 119.9(2)
C5 C4 C3 122.5(2)
C9 C4 C3 119.5(2)
C9 C4 C5 117.9(2)
C4 C5 H5 118.8(19)
C6 C5 C4 120.5(2)
C6 C5 H5 120.7(19)
C5 C6 C7 120.9(2)
C5 C6 H6 120(2)
C7 C6 H6 119(2)
C6 C7 H7 120.8(19)
C8 C7 C6 119.8(2)
C8 C7 H7 119.4(19)
C7 C8 C9 119.6(2)
C7 C8 H8 121.9(18)
C9 C8 H8 118.5(18)
C4 C9 C1 120.1(2)
C8 C9 C1 118.6(2)
C8 C9 C4 121.2(2)
C3 C10 C11 119.9(2)
C3 C10 C12 120.2(2)
C3 C10 H10 114.2(19)
C11 C10 H10 116.3(19)
C12 C10 C11 59.47(18)
C12 C10 H10 116.1(19)
C10 C11 H11A 118.0(19)
C10 C11 H11B 118(2)
C12 C11 C10 59.95(18)
C12 C11 H11A 118(2)
C12 C11 H11B 119(2)
H11A C11 H11B 114(3)
C10 C12 H12A 119(2)
C10 C12 H12B 115(2)
C11 C12 C10 60.59(18)
C11 C12 H12A 118(2)
C11 C12 H12B 117(2)
H12A C12 H12B 116(3)
C14 C13 C2 120.5(2)
C18 C13 C2 120.6(2)
C18 C13 C14 118.9(2)
C13 C14 H14 120(2)
C15 C14 C13 119.8(2)
C15 C14 H14 120(2)
C14 C15 C16 121.3(2)
C14 C15 C19 119.7(2)
C16 C15 C19 119.0(2)
C15 C16 H16 121(2)
C17 C16 C15 118.9(2)
C17 C16 H16 120(2)
C16 C17 C18 120.6(2)
C16 C17 H17 120(2)
C18 C17 H17 119(2)
C13 C18 H18 118.9(18)
C17 C18 C13 120.5(2)
C17 C18 H18 120.4(18)
F1 C19 F2A 89.6(4)
F1 C19 F2B 65.9(6)
F1 C19 F3 102.9(3)
F1 C19 C15 113.8(3)
F1A C19 F1 20.6(3)
F1A C19 F2A 106.6(4)
F1A C19 F2B 85.7(7)
F1A C19 F3 83.4(4)
F1A C19 F3A 105.6(5)
F1A C19 F3B 129.4(5)
F1A C19 C15 115.9(3)
F1B C19 F1 50.8(8)
F1B C19 F1A 30.2(7)
F1B C19 F2A 128.2(8)
F1B C19 F2B 114.3(10)
F1B C19 F3 54.2(8)
F1B C19 F3A 80.1(8)
F1B C19 F3B 114.0(9)
F1B C19 C15 114.5(7)
F2 C19 F1 109.9(4)
F2 C19 F1A 121.5(4)
F2 C19 F1B 129.8(7)
F2 C19 F2A 26.7(3)
F2 C19 F2B 56.1(6)
F2 C19 F3 103.5(4)
F2 C19 F3A 75.5(4)
F2 C19 F3B 38.9(5)
F2 C19 C15 115.5(3)
F2A C19 F2B 29.5(5)
F2A C19 F3 126.5(4)
F2A C19 C15 111.6(3)
F2B C19 F3 145.5(6)
F2B C19 C15 104.2(6)
F3 C19 C15 110.0(3)
F3A C19 F1 121.3(4)
F3A C19 F2A 100.9(5)
F3A C19 F2B 127.5(7)
F3A C19 F3 29.4(3)
F3A C19 C15 115.0(4)
F3B C19 F1 132.4(5)
F3B C19 F2A 65.6(5)
F3B C19 F2B 94.9(8)
F3B C19 F3 68.1(5)
F3B C19 F3A 38.7(5)
F3B C19 C15 113.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C19 1.362(4)
F1A C19 1.336(4)
F1B C19 1.336(5)
F2 C19 1.315(3)
F2A C19 1.364(4)
F2B C19 1.366(5)
F3 C19 1.373(4)
F3A C19 1.351(4)
F3B C19 1.347(4)
O1 C1 1.367(3)
O1 C2 1.389(3)
O2 C1 1.210(3)
C1 C9 1.462(3)
C2 C3 1.348(3)
C2 C13 1.476(3)
C3 C4 1.455(3)
C3 C10 1.495(3)
C4 C5 1.406(3)
C4 C9 1.404(3)
C5 C6 1.381(4)
C5 H5 1.00(3)
C6 C7 1.395(4)
C6 H6 0.96(4)
C7 C8 1.379(4)
C7 H7 0.99(3)
C8 C9 1.401(3)
C8 H8 0.97(3)
C10 C11 1.517(4)
C10 C12 1.507(4)
C10 H10 0.98(3)
C11 C12 1.500(4)
C11 H11A 0.99(3)
C11 H11B 0.99(4)
C12 H12A 0.93(4)
C12 H12B 1.02(4)
C13 C14 1.399(3)
C13 C18 1.398(3)
C14 C15 1.385(4)
C14 H14 0.95(4)
C15 C16 1.388(4)
C15 C19 1.494(4)
C16 C17 1.387(4)
C16 H16 0.97(4)
C17 C18 1.388(4)
C17 H17 0.99(4)
C18 H18 0.96(3)
