#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:32:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178395 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/17/4021745.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_4021745
loop_
_publ_author_name
'Vyacheslav Ya. Sosnovskikh'
'Vladislav Yu. Korotaev'
'Dmitry L. Chizhov'
'Igor B. Kutyashev'
'Danil S. Yachevskii'
'Olga N. Kazheva'
'Oleg A. Dyachenko'
'Valery N. Charushin'
_publ_contact_author             'Olga Kazheva'
_publ_contact_author_email       koh@ipc.ac.ru
_publ_section_title
;
 Reaction of Polyhaloalkyl-Substituted Chromones, Pyrones,
 and Furanones with Salicylaldehydes as a Direct Route
 to Fused 2H-Chromenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4538
_journal_page_last               4543
_journal_paper_doi               10.1021/jo060459x
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C21 H10 F6 O4'
_chemical_formula_weight         440.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-11-07T17:13:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.37(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.053(2)
_cell_length_b                   12.222(2)
_cell_length_c                   13.902(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1862.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3392
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.57
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_refine_diff_density_max         0.13
_refine_diff_density_min         0.163
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0010(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.1864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2545
_reflns_number_total             3217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060459xsi20060303_121732.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021745
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
F1 F 0.26930(12) 0.56534(11) 0.15343(9) 0.0929(4) Uani 1 1 d .
F2 F 0.08951(10) 0.52458(9) 0.18340(10) 0.0908(4) Uani 1 1 d .
F3 F 0.18950(12) 0.65221(9) 0.26343(9) 0.0893(4) Uani 1 1 d .
F4 F 0.23216(10) 0.25421(11) 0.08717(7) 0.0843(4) Uani 1 1 d .
F5 F 0.06262(9) 0.30503(10) 0.13082(8) 0.0820(3) Uani 1 1 d .
F6 F 0.12099(11) 0.13910(9) 0.15166(8) 0.0803(3) Uani 1 1 d .
O1 O 0.36922(9) 0.50703(9) 0.33788(8) 0.0530(3) Uani 1 1 d .
O3 O 0.27314(10) 0.37685(8) 0.24433(8) 0.0536(3) Uani 1 1 d .
O5 O 0.32733(9) 0.20283(9) 0.27471(8) 0.0506(3) Uani 1 1 d .
O7 O -0.01128(11) 0.35974(11) 0.40368(11) 0.0763(4) Uani 1 1 d .
C1 C 0.19989(16) 0.55396(15) 0.22389(13) 0.0630(4) Uani 1 1 d .
C2 C 0.25211(12) 0.46951(12) 0.30012(11) 0.0463(3) Uani 1 1 d .
C3 C 0.15920(15) 0.24283(15) 0.15530(12) 0.0585(4) Uani 1 1 d .
C4 C 0.22457(12) 0.27238(12) 0.25710(11) 0.0447(3) Uani 1 1 d .
C6 C 0.31063(14) 0.09925(13) 0.31197(11) 0.0515(4) Uani 1 1 d .
C7 C 0.40063(19) 0.02313(16) 0.30418(14) 0.0715(5) Uani 1 1 d .
H7 H 0.4689 0.0413 0.2748 0.095(7) Uiso 1 1 calc R
C8 C 0.3878(2) -0.08050(18) 0.34066(18) 0.0916(7) Uani 1 1 d .
H8 H 0.4476 -0.1329 0.3351 0.105(8) Uiso 1 1 calc R
C9 C 0.2877(2) -0.10734(18) 0.38512(18) 0.0924(7) Uani 1 1 d .
H9 H 0.2786 -0.1782 0.4075 0.090(7) Uiso 1 1 calc R
C10 C 0.2010(2) -0.02939(16) 0.39645(15) 0.0748(5) Uani 1 1 d .
H10 H 0.1354 -0.047 0.4292 0.071(6) Uiso 1 1 calc R
C11 C 0.21057(14) 0.07589(13) 0.35929(12) 0.0533(4) Uani 1 1 d .
C12 C 0.12975(13) 0.16524(13) 0.37449(11) 0.0508(4) Uani 1 1 d .
H12 H 0.0699 0.155 0.4149 0.050(4) Uiso 1 1 calc R
C13 C 0.13882(12) 0.26231(12) 0.33190(11) 0.0448(3) Uani 1 1 d .
C14 C 0.08363(14) 0.36100(13) 0.36914(12) 0.0522(4) Uani 1 1 d .
C15 C 0.16878(13) 0.45417(12) 0.37601(11) 0.0474(4) Uani 1 1 d .
C16 C 0.18566(13) 0.51560(12) 0.45675(12) 0.0507(4) Uani 1 1 d .
H16 H 0.1281 0.5132 0.5 0.066(5) Uiso 1 1 calc R
C17 C 0.29077(13) 0.58487(12) 0.47772(11) 0.0487(4) Uani 1 1 d .
C18 C 0.31220(16) 0.65082(14) 0.56028(13) 0.0606(4) Uani 1 1 d .
H18 H 0.2529 0.657 0.6018 0.069(5) Uiso 1 1 calc R
C19 C 0.42054(16) 0.70658(15) 0.58049(14) 0.0672(5) Uani 1 1 d .
H19 H 0.4345 0.7507 0.6353 0.091(7) Uiso 1 1 calc R
C20 C 0.50836(15) 0.69683(15) 0.51909(14) 0.0645(5) Uani 1 1 d .
H20 H 0.5813 0.7349 0.533 0.078(6) Uiso 1 1 calc R
C21 C 0.49059(14) 0.63190(14) 0.43746(13) 0.0574(4) Uani 1 1 d .
H21 H 0.5508 0.6256 0.3968 0.075(6) Uiso 1 1 calc R
C22 C 0.38191(13) 0.57655(12) 0.41747(11) 0.0475(3) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C22 O1 C2 119.35(11)
C4 O3 C2 124.63(11)
C6 O5 C4 118.03(11)
F2 C1 F1 107.62(16)
F2 C1 F3 107.22(15)
F1 C1 F3 107.39(15)
F2 C1 C2 110.76(14)
F1 C1 C2 112.19(14)
F3 C1 C2 111.43(14)
O3 C2 O1 104.95(11)
O3 C2 C15 116.54(12)
O1 C2 C15 113.36(12)
O3 C2 C1 103.53(13)
O1 C2 C1 106.49(12)
C15 C2 C1 111.03(13)
F5 C3 F4 107.52(15)
F5 C3 F6 107.21(14)
F4 C3 F6 106.89(14)
F5 C3 C4 111.65(13)
F4 C3 C4 111.90(14)
F6 C3 C4 111.39(14)
O3 C4 O5 104.86(11)
O3 C4 C13 116.62(12)
O5 C4 C13 113.30(12)
O3 C4 C3 103.75(12)
O5 C4 C3 106.77(11)
C13 C4 C3 110.66(12)
C7 C6 C11 121.76(16)
C7 C6 O5 117.05(15)
C11 C6 O5 121.10(14)
C6 C7 C8 118.9(2)
C9 C8 C7 120.7(2)
C10 C9 C8 120.0(2)
C9 C10 C11 120.7(2)
C6 C11 C10 117.91(16)
C6 C11 C12 117.38(14)
C10 C11 C12 124.45(17)
C13 C12 C11 121.60(14)
C12 C13 C14 120.85(14)
C12 C13 C4 118.08(13)
C14 C13 C4 120.20(13)
O7 C14 C15 124.35(14)
O7 C14 C13 123.24(14)
C15 C14 C13 111.43(12)
C16 C15 C14 120.36(14)
C16 C15 C2 119.09(14)
C14 C15 C2 119.77(13)
C15 C16 C17 121.39(14)
C22 C17 C18 118.43(14)
C22 C17 C16 117.57(14)
C18 C17 C16 123.63(14)
C19 C18 C17 120.33(16)
C18 C19 C20 119.66(17)
C19 C20 C21 121.52(16)
C22 C21 C20 118.56(16)
C21 C22 O1 117.29(13)
C21 C22 C17 121.49(15)
O1 C22 C17 121.12(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.327(2)
F2 C1 1.326(2)
F3 C1 1.332(2)
F4 C3 1.328(2)
F5 C3 1.3192(18)
F6 C3 1.335(2)
O1 C22 1.3877(18)
O1 C2 1.4097(17)
O3 C4 1.4053(18)
O3 C2 1.4087(18)
O5 C6 1.3891(19)
O5 C4 1.4147(17)
O7 C14 1.2085(18)
C1 C2 1.538(2)
C2 C15 1.499(2)
C3 C4 1.547(2)
C4 C13 1.499(2)
C6 C7 1.376(2)
C6 C11 1.387(2)
C7 C8 1.378(3)
C8 C9 1.375(3)
C9 C10 1.374(3)
C10 C11 1.396(3)
C11 C12 1.443(2)
C12 C13 1.335(2)
C13 C14 1.475(2)
C14 C15 1.473(2)
C15 C16 1.343(2)
C16 C17 1.437(2)
C17 C22 1.394(2)
C17 C18 1.398(2)
C18 C19 1.375(2)
C19 C20 1.378(3)
C20 C21 1.378(3)
C21 C22 1.376(2)
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
C4 O3 C2 O1 124.42(13)
C4 O3 C2 C15 -1.9(2)
C4 O3 C2 C1 -124.08(14)
C22 O1 C2 O3 -161.31(12)
C22 O1 C2 C15 -33.07(18)
C22 O1 C2 C1 89.32(15)
F2 C1 C2 O3 68.95(17)
F1 C1 C2 O3 -51.33(17)
F3 C1 C2 O3 -171.78(13)
F2 C1 C2 O1 179.32(14)
F1 C1 C2 O1 59.04(17)
F3 C1 C2 O1 -61.41(17)
F2 C1 C2 C15 -56.84(19)
F1 C1 C2 C15 -177.12(14)
F3 C1 C2 C15 62.43(18)
C2 O3 C4 O5 -122.51(13)
C2 O3 C4 C13 3.7(2)
C2 O3 C4 C3 125.63(14)
C6 O5 C4 O3 165.48(11)
C6 O5 C4 C13 37.23(17)
C6 O5 C4 C3 -84.84(15)
F5 C3 C4 O3 -68.26(16)
F4 C3 C4 O3 52.32(16)
F6 C3 C4 O3 171.91(12)
F5 C3 C4 O5 -178.72(13)
F4 C3 C4 O5 -58.14(17)
F6 C3 C4 O5 61.45(16)
F5 C3 C4 C13 57.55(18)
F4 C3 C4 C13 178.14(13)
F6 C3 C4 C13 -62.27(16)
C4 O5 C6 C7 162.85(14)
C4 O5 C6 C11 -20.4(2)
C11 C6 C7 C8 3.0(3)
O5 C6 C7 C8 179.70(18)
C6 C7 C8 C9 -0.7(4)
C7 C8 C9 C10 -2.2(4)
C8 C9 C10 C11 3.0(4)
C7 C6 C11 C10 -2.2(3)
O5 C6 C11 C10 -178.80(15)
C7 C6 C11 C12 172.14(16)
O5 C6 C11 C12 -4.5(2)
C9 C10 C11 C6 -0.8(3)
C9 C10 C11 C12 -174.70(18)
C6 C11 C12 C13 10.4(2)
C10 C11 C12 C13 -175.66(16)
C11 C12 C13 C14 -161.35(14)
C11 C12 C13 C4 8.0(2)
O3 C4 C13 C12 -153.19(13)
O5 C4 C13 C12 -31.31(18)
C3 C4 C13 C12 88.57(16)
O3 C4 C13 C14 16.2(2)
O5 C4 C13 C14 138.07(13)
C3 C4 C13 C14 -102.06(16)
C12 C13 C14 O7 -35.2(2)
C4 C13 C14 O7 155.76(16)
C12 C13 C14 C15 133.95(15)
C4 C13 C14 C15 -35.1(2)
O7 C14 C15 C16 36.1(3)
C13 C14 C15 C16 -132.85(15)
O7 C14 C15 C2 -154.04(17)
C13 C14 C15 C2 37.0(2)
O3 C2 C15 C16 150.01(14)
O1 C2 C15 C16 28.01(19)
C1 C2 C15 C16 -91.82(17)
O3 C2 C15 C14 -20.0(2)
O1 C2 C15 C14 -141.95(14)
C1 C2 C15 C14 98.22(17)
C14 C15 C16 C17 161.60(14)
C2 C15 C16 C17 -8.3(2)
C15 C16 C17 C22 -7.4(2)
C15 C16 C17 C18 179.58(15)
C22 C17 C18 C19 0.6(2)
C16 C17 C18 C19 173.48(16)
C17 C18 C19 C20 -0.3(3)
C18 C19 C20 C21 -0.2(3)
C19 C20 C21 C22 0.4(3)
C20 C21 C22 O1 -176.47(15)
C20 C21 C22 C17 -0.1(2)
C2 O1 C22 C21 -164.61(14)
C2 O1 C22 C17 19.0(2)
C18 C17 C22 C21 -0.4(2)
C16 C17 C22 C21 -173.74(14)
C18 C17 C22 O1 175.88(14)
C16 C17 C22 O1 2.5(2)
