#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178481 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/02/4030222.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_4030222
loop_
_publ_author_name
'Smirnov, Vladimir O.'
'Struchkova, Marina I.'
'Arkhipov, Dmitry E.'
'Korlyukov, Alexander A.'
'Dilman, Alexander D.'
_publ_section_title
;
 Synthesis of gem-difluorinated nitroso compounds.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11819
_journal_page_last               11823
_journal_paper_doi               10.1021/jo5023537
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C24 H19 F2 N O4'
_chemical_formula_sum            'C24 H19 F2 N O4'
_chemical_formula_weight         423.40
_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                81.8040(10)
_cell_angle_beta                 69.6860(10)
_cell_angle_gamma                82.9050(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5372(6)
_cell_length_b                   10.4431(7)
_cell_length_c                   12.2360(8)
_cell_measurement_reflns_used    3486
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.79
_cell_measurement_theta_min      2.52
_cell_volume                     1009.37(12)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13079
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0450
_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)+(0.0419P)²+0.3057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                4451
_reflns_number_total             5880
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            jo5023537_si_003.cif
_cod_data_source_block           sv36
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030221--4030222.cif.
;
_cod_original_cell_volume        1009.38(12)
_cod_database_code               4030222
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
F1 F 0.48197(10) 0.49823(8) 0.15801(7) 0.02500(19) Uani 1 1 d .
F2 F 0.55040(10) 0.64610(7) 0.23502(8) 0.02620(19) Uani 1 1 d .
O1 O 0.80688(11) 0.44187(9) 0.14034(8) 0.0201(2) Uani 1 1 d .
O2 O 0.61489(12) 0.23936(9) 0.36266(8) 0.0229(2) Uani 1 1 d .
O3 O -0.21882(12) 0.95195(9) 0.44304(9) 0.0259(2) Uani 1 1 d .
O4 O -0.30589(12) 0.82229(9) 0.34768(9) 0.0247(2) Uani 1 1 d .
N1 N 0.67279(13) 0.44500(11) 0.25438(10) 0.0190(2) Uani 1 1 d .
C1 C 0.69255(15) 0.30973(12) 0.28155(11) 0.0167(2) Uani 1 1 d .
C2 C 0.84243(15) 0.30071(12) 0.16848(11) 0.0161(2) Uani 1 1 d .
C3 C 0.51991(16) 0.51868(12) 0.25296(12) 0.0190(3) Uani 1 1 d .
C4 C 0.37657(17) 0.48667(14) 0.36534(12) 0.0226(3) Uani 1 1 d .
H4A H 0.3479 0.3969 0.3683 0.027 Uiso 1 1 calc R
H4B H 0.4124 0.4911 0.4334 0.027 Uiso 1 1 calc R
C5 C 0.22297(16) 0.57949(13) 0.37364(11) 0.0202(3) Uani 1 1 d .
C6 C 0.20736(17) 0.69644(13) 0.42030(12) 0.0218(3) Uani 1 1 d .
H6A H 0.2910 0.7157 0.4489 0.026 Uiso 1 1 calc R
C7 C 0.07052(17) 0.78476(13) 0.42522(12) 0.0208(3) Uani 1 1 d .
H7A H 0.0618 0.8651 0.4556 0.025 Uiso 1 1 calc R
C8 C -0.05424(16) 0.75585(12) 0.38573(11) 0.0192(3) Uani 1 1 d .
C9 C -0.04053(17) 0.63827(13) 0.34045(12) 0.0224(3) Uani 1 1 d .
H9A H -0.1259 0.6180 0.3139 0.027 Uiso 1 1 calc R
C10 C 0.09826(17) 0.55068(13) 0.33410(12) 0.0232(3) Uani 1 1 d .
H10A H 0.1079 0.4708 0.3026 0.028 Uiso 1 1 calc R
C11 C -0.19975(16) 0.85434(13) 0.39586(12) 0.0200(3) Uani 1 1 d .
C12 C -0.45512(17) 0.91101(13) 0.36040(13) 0.0246(3) Uani 1 1 d .
H12A H -0.5127 0.8910 0.3089 0.037 Uiso 1 1 calc R
H12B H -0.4229 1.0004 0.3390 0.037 Uiso 1 1 calc R
H12C H -0.5303 0.9013 0.4419 0.037 Uiso 1 1 calc R
C13 C 0.80979(15) 0.22041(12) 0.08598(11) 0.0172(2) Uani 1 1 d .
C14 C 0.81312(17) 0.08640(13) 0.11454(12) 0.0222(3) Uani 1 1 d .
H14A H 0.8403 0.0483 0.1816 0.027 Uiso 1 1 calc R
C15 C 0.77689(19) 0.00880(15) 0.04516(14) 0.0296(3) Uani 1 1 d .
H15A H 0.7766 -0.0824 0.0656 0.036 Uiso 1 1 calc R
C16 C 0.74093(19) 0.06418(17) -0.05426(14) 0.0331(4) Uani 1 1 d .
H16A H 0.7156 0.0109 -0.1017 0.040 Uiso 1 1 calc R
C17 C 0.74188(19) 0.19691(17) -0.08430(13) 0.0308(3) Uani 1 1 d .
H17A H 0.7203 0.2341 -0.1537 0.037 Uiso 1 1 calc R
C18 C 0.77425(17) 0.27658(14) -0.01377(12) 0.0237(3) Uani 1 1 d .
H18A H 0.7721 0.3680 -0.0335 0.028 Uiso 1 1 calc R
C19 C 1.01386(15) 0.27036(12) 0.17921(11) 0.0170(2) Uani 1 1 d .
C20 C 1.15129(16) 0.31739(13) 0.08770(12) 0.0210(3) Uani 1 1 d .
H20A H 1.1352 0.3693 0.0215 0.025 Uiso 1 1 calc R
C21 C 1.31114(17) 0.28841(14) 0.09340(13) 0.0245(3) Uani 1 1 d .
H21A H 1.4048 0.3208 0.0313 0.029 Uiso 1 1 calc R
C22 C 1.33461(17) 0.21181(14) 0.19006(13) 0.0242(3) Uani 1 1 d .
H22A H 1.4444 0.1918 0.1937 0.029 Uiso 1 1 calc R
C23 C 1.19843(17) 0.16452(13) 0.28114(12) 0.0225(3) Uani 1 1 d .
H23A H 1.2150 0.1123 0.3471 0.027 Uiso 1 1 calc R
C24 C 1.03709(16) 0.19366(13) 0.27581(11) 0.0199(3) Uani 1 1 d .
H24A H 0.9435 0.1612 0.3379 0.024 Uiso 1 1 calc R
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 O1 C2 89.66(8)
C11 O4 C12 115.22(11)
C1 N1 C3 125.77(11)
C1 N1 O1 92.64(9)
C3 N1 O1 115.56(10)
O2 C1 N1 131.14(12)
O2 C1 C2 138.73(12)
N1 C1 C2 90.12(9)
O1 C2 C19 111.64(10)
O1 C2 C13 112.35(10)
C19 C2 C13 113.55(10)
O1 C2 C1 87.28(9)
C19 C2 C1 117.69(10)
C13 C2 C1 111.64(10)
F2 C3 F1 104.65(10)
F2 C3 N1 106.94(10)
F1 C3 N1 110.50(10)
F2 C3 C4 112.47(11)
F1 C3 C4 110.77(11)
N1 C3 C4 111.26(11)
C5 C4 C3 111.56(11)
C5 C4 H4A 109.3
C3 C4 H4A 109.3
C5 C4 H4B 109.3
C3 C4 H4B 109.3
H4A C4 H4B 108.0
C10 C5 C6 119.51(12)
C10 C5 C4 121.11(12)
C6 C5 C4 119.38(12)
C7 C6 C5 120.38(13)
C7 C6 H6A 119.8
C5 C6 H6A 119.8
C6 C7 C8 120.08(12)
C6 C7 H7A 120.0
C8 C7 H7A 120.0
C7 C8 C9 119.82(12)
C7 C8 C11 117.20(12)
C9 C8 C11 122.98(12)
C10 C9 C8 119.91(13)
C10 C9 H9A 120.0
C8 C9 H9A 120.0
C9 C10 C5 120.29(13)
C9 C10 H10A 119.9
C5 C10 H10A 119.9
O3 C11 O4 124.02(12)
O3 C11 C8 123.34(12)
O4 C11 C8 112.64(11)
O4 C12 H12A 109.5
O4 C12 H12B 109.5
H12A C12 H12B 109.5
O4 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C18 C13 C14 120.32(12)
C18 C13 C2 122.18(12)
C14 C13 C2 117.50(11)
C15 C14 C13 119.97(13)
C15 C14 H14A 120.0
C13 C14 H14A 120.0
C14 C15 C16 120.01(14)
C14 C15 H15A 120.0
C16 C15 H15A 120.0
C17 C16 C15 120.02(14)
C17 C16 H16A 120.0
C15 C16 H16A 120.0
C16 C17 C18 120.60(14)
C16 C17 H17A 119.7
C18 C17 H17A 119.7
C13 C18 C17 119.05(14)
C13 C18 H18A 120.5
C17 C18 H18A 120.5
C24 C19 C20 120.14(12)
C24 C19 C2 121.33(11)
C20 C19 C2 118.49(11)
C21 C20 C19 119.96(13)
C21 C20 H20A 120.0
C19 C20 H20A 120.0
C20 C21 C22 119.97(13)
C20 C21 H21A 120.0
C22 C21 H21A 120.0
C23 C22 C21 120.29(13)
C23 C22 H22A 119.9
C21 C22 H22A 119.9
C22 C23 C24 119.92(13)
C22 C23 H23A 120.0
C24 C23 H23A 120.0
C19 C24 C23 119.71(12)
C19 C24 H24A 120.1
C23 C24 H24A 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.3599(15)
F2 C3 1.3598(15)
O1 N1 1.4674(14)
O1 C2 1.4836(15)
O2 C1 1.1917(15)
O3 C11 1.2084(16)
O4 C11 1.3352(16)
O4 C12 1.4552(16)
N1 C1 1.4074(16)
N1 C3 1.4352(16)
C1 C2 1.5292(18)
C2 C19 1.5056(17)
C2 C13 1.5147(18)
C3 C4 1.5171(19)
C4 C5 1.5136(18)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C10 1.3915(19)
C5 C6 1.3933(19)
C6 C7 1.3856(19)
C6 H6A 0.9500
C7 C8 1.3920(19)
C7 H7A 0.9500
C8 C9 1.3935(18)
C8 C11 1.4933(18)
C9 C10 1.3912(19)
C9 H9A 0.9500
C10 H10A 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C18 1.3910(19)
C13 C14 1.3926(18)
C14 C15 1.383(2)
C14 H14A 0.9500
C15 C16 1.387(2)
C15 H15A 0.9500
C16 C17 1.383(2)
C16 H16A 0.9500
C17 C18 1.393(2)
C17 H17A 0.9500
C18 H18A 0.9500
C19 C24 1.3898(18)
C19 C20 1.3946(18)
C20 C21 1.3845(19)
C20 H20A 0.9500
C21 C22 1.391(2)
C21 H21A 0.9500
C22 C23 1.387(2)
C22 H22A 0.9500
C23 C24 1.3954(18)
C23 H23A 0.9500
C24 H24A 0.9500
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
C2 O1 N1 C1 -4.30(9)
C2 O1 N1 C3 -136.43(11)
C3 N1 C1 O2 -50.8(2)
O1 N1 C1 O2 -175.20(14)
C3 N1 C1 C2 128.62(12)
O1 N1 C1 C2 4.18(9)
N1 O1 C2 C19 -114.83(10)
N1 O1 C2 C13 116.27(10)
N1 O1 C2 C1 3.96(9)
O2 C1 C2 O1 175.16(17)
N1 C1 C2 O1 -4.13(9)
O2 C1 C2 C19 -71.8(2)
N1 C1 C2 C19 108.95(11)
O2 C1 C2 C13 62.2(2)
N1 C1 C2 C13 -117.13(11)
C1 N1 C3 F2 173.58(11)
O1 N1 C3 F2 -72.36(13)
C1 N1 C3 F1 -73.08(15)
O1 N1 C3 F1 40.97(14)
C1 N1 C3 C4 50.41(17)
O1 N1 C3 C4 164.46(10)
F2 C3 C4 C5 50.34(15)
F1 C3 C4 C5 -66.37(14)
N1 C3 C4 C5 170.29(11)
C3 C4 C5 C10 93.01(15)
C3 C4 C5 C6 -86.17(15)
C10 C5 C6 C7 -1.3(2)
C4 C5 C6 C7 177.88(12)
C5 C6 C7 C8 1.4(2)
C6 C7 C8 C9 -0.5(2)
C6 C7 C8 C11 178.80(12)
C7 C8 C9 C10 -0.5(2)
C11 C8 C9 C10 -179.69(13)
C8 C9 C10 C5 0.5(2)
C6 C5 C10 C9 0.4(2)
C4 C5 C10 C9 -178.80(13)
C12 O4 C11 O3 -2.96(19)
C12 O4 C11 C8 176.79(11)
C7 C8 C11 O3 -5.0(2)
C9 C8 C11 O3 174.21(13)
C7 C8 C11 O4 175.22(11)
C9 C8 C11 O4 -5.54(18)
O1 C2 C13 C18 8.62(16)
C19 C2 C13 C18 -119.28(13)
C1 C2 C13 C18 104.82(13)
O1 C2 C13 C14 -170.11(10)
C19 C2 C13 C14 61.99(15)
C1 C2 C13 C14 -73.91(14)
C18 C13 C14 C15 -1.61(19)
C2 C13 C14 C15 177.15(12)
C13 C14 C15 C16 1.4(2)
C14 C15 C16 C17 0.2(2)
C15 C16 C17 C18 -1.8(2)
C14 C13 C18 C17 0.10(19)
C2 C13 C18 C17 -178.59(12)
C16 C17 C18 C13 1.6(2)
O1 C2 C19 C24 129.75(12)
C13 C2 C19 C24 -101.99(14)
C1 C2 C19 C24 31.09(17)
O1 C2 C19 C20 -52.41(15)
C13 C2 C19 C20 75.85(14)
C1 C2 C19 C20 -151.07(12)
C24 C19 C20 C21 -0.5(2)
C2 C19 C20 C21 -178.31(12)
C19 C20 C21 C22 0.4(2)
C20 C21 C22 C23 -0.2(2)
C21 C22 C23 C24 0.1(2)
C20 C19 C24 C23 0.36(19)
C2 C19 C24 C23 178.16(12)
C22 C23 C24 C19 -0.2(2)
