#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178481 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/02/4030221.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_4030221
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         'C15 H11 F2 N O3'
_chemical_formula_sum            'C15 H11 F2 N O3'
_chemical_formula_weight         291.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.501(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.830(2)
_cell_length_b                   5.1326(7)
_cell_length_c                   17.275(2)
_cell_measurement_reflns_used    3018
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.11
_cell_measurement_theta_min      2.47
_cell_volume                     1338.6(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11699
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0459
_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)+(0.0591P)²+0.2054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                1812
_reflns_number_total             2620
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            jo5023537_si_002.cif
_cod_data_source_block           sv74
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               4030221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.92232(10) 0.9017(3) 0.08606(10) 0.0594(4) Uani 1 1 d .
F2 F 0.90335(9) 0.5241(3) 0.02856(8) 0.0551(4) Uani 1 1 d .
O1 O 1.05676(13) 0.4018(4) 0.12271(12) 0.0673(6) Uani 1 1 d .
O2 O 0.52865(9) 0.7691(3) 0.09635(8) 0.0294(4) Uani 1 1 d .
O3 O 0.52706(10) 0.5093(3) 0.20007(9) 0.0451(4) Uani 1 1 d .
N1 N 1.03536(14) 0.6160(5) 0.13156(13) 0.0536(6) Uani 1 1 d .
C1 C 0.93520(14) 0.6438(5) 0.10055(13) 0.0378(5) Uani 1 1 d .
C2 C 0.89428(13) 0.5457(4) 0.16197(12) 0.0302(5) Uani 1 1 d .
H2A H 0.9258 0.6229 0.2154 0.036 Uiso 1 1 calc R
H2B H 0.9021 0.3544 0.1667 0.036 Uiso 1 1 calc R
C3 C 0.79696(13) 0.6079(4) 0.14184(11) 0.0263(5) Uani 1 1 d .
C4 C 0.76896(13) 0.8228(4) 0.17552(11) 0.0270(5) Uani 1 1 d .
H4A H 0.8116 0.9362 0.2096 0.032 Uiso 1 1 calc R
C5 C 0.68029(13) 0.8754(4) 0.16057(11) 0.0282(5) Uani 1 1 d .
H5A H 0.6617 1.0235 0.1841 0.034 Uiso 1 1 calc R
C6 C 0.61896(12) 0.7104(4) 0.11098(11) 0.0260(5) Uani 1 1 d .
C7 C 0.64403(13) 0.4993(4) 0.07450(11) 0.0287(5) Uani 1 1 d .
H7A H 0.6008 0.3897 0.0394 0.034 Uiso 1 1 calc R
C8 C 0.73350(13) 0.4486(4) 0.08969(12) 0.0285(5) Uani 1 1 d .
H8A H 0.7518 0.3040 0.0644 0.034 Uiso 1 1 calc R
C9 C 0.48991(13) 0.6652(4) 0.14959(11) 0.0290(5) Uani 1 1 d .
C10 C 0.39940(13) 0.7675(4) 0.13766(11) 0.0270(5) Uani 1 1 d .
C11 C 0.36600(14) 0.9760(4) 0.08652(12) 0.0310(5) Uani 1 1 d .
H11A H 0.4013 1.0585 0.0579 0.037 Uiso 1 1 calc R
C12 C 0.28093(15) 1.0629(4) 0.07748(13) 0.0386(6) Uani 1 1 d .
H12A H 0.2579 1.2063 0.0428 0.046 Uiso 1 1 calc R
C13 C 0.22951(15) 0.9431(4) 0.11832(14) 0.0399(6) Uani 1 1 d .
H13A H 0.1709 1.0026 0.1113 0.048 Uiso 1 1 calc R
C14 C 0.26279(15) 0.7362(5) 0.16966(14) 0.0414(6) Uani 1 1 d .
H14A H 0.2272 0.6543 0.1981 0.050 Uiso 1 1 calc R
C15 C 0.34759(14) 0.6491(4) 0.17953(13) 0.0357(5) Uani 1 1 d .
H15A H 0.3707 0.5077 0.2151 0.043 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
C9 O2 C6 115.81(14)
O1 N1 C1 110.7(2)
F2 C1 F1 106.44(19)
F2 C1 C2 112.54(18)
F1 C1 C2 112.95(19)
F2 C1 N1 110.19(18)
F1 C1 N1 103.91(18)
C2 C1 N1 110.41(18)
C1 C2 C3 113.43(17)
C1 C2 H2A 108.9
C3 C2 H2A 108.9
C1 C2 H2B 108.9
C3 C2 H2B 108.9
H2A C2 H2B 107.7
C4 C3 C8 118.70(19)
C4 C3 C2 120.48(18)
C8 C3 C2 120.81(18)
C5 C4 C3 121.10(19)
C5 C4 H4A 119.5
C3 C4 H4A 119.5
C6 C5 C4 119.02(19)
C6 C5 H5A 120.5
C4 C5 H5A 120.5
C7 C6 C5 121.68(19)
C7 C6 O2 120.37(17)
C5 C6 O2 117.92(17)
C6 C7 C8 118.83(18)
C6 C7 H7A 120.6
C8 C7 H7A 120.6
C7 C8 C3 120.61(19)
C7 C8 H8A 119.7
C3 C8 H8A 119.7
O3 C9 O2 122.11(18)
O3 C9 C10 125.45(19)
O2 C9 C10 112.44(16)
C11 C10 C15 119.90(19)
C11 C10 C9 121.97(18)
C15 C10 C9 118.13(18)
C12 C11 C10 119.5(2)
C12 C11 H11A 120.2
C10 C11 H11A 120.2
C13 C12 C11 120.4(2)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C12 C13 C14 120.2(2)
C12 C13 H13A 119.9
C14 C13 H13A 119.9
C15 C14 C13 119.9(2)
C15 C14 H14A 120.1
C13 C14 H14A 120.1
C14 C15 C10 120.1(2)
C14 C15 H15A 120.0
C10 C15 H15A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.351(3)
F2 C1 1.342(2)
O1 N1 1.174(3)
O2 C9 1.358(2)
O2 C6 1.408(2)
O3 C9 1.199(2)
N1 C1 1.520(3)
C1 C2 1.487(3)
C2 C3 1.508(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.381(3)
C3 C8 1.395(3)
C4 C5 1.375(3)
C4 H4A 0.9500
C5 C6 1.376(3)
C5 H5A 0.9500
C6 C7 1.371(3)
C7 C8 1.385(3)
C7 H7A 0.9500
C8 H8A 0.9500
C9 C10 1.481(3)
C10 C11 1.387(3)
C10 C15 1.386(3)
C11 C12 1.382(3)
C11 H11A 0.9500
C12 C13 1.372(3)
C12 H12A 0.9500
C13 C14 1.382(3)
C13 H13A 0.9500
C14 C15 1.376(3)
C14 H14A 0.9500
C15 H15A 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
O1 N1 C1 F2 -44.3(3)
O1 N1 C1 F1 -158.0(2)
O1 N1 C1 C2 80.6(3)
F2 C1 C2 C3 -66.2(2)
F1 C1 C2 C3 54.4(3)
N1 C1 C2 C3 170.23(18)
C1 C2 C3 C4 -96.7(2)
C1 C2 C3 C8 84.0(2)
C8 C3 C4 C5 2.2(3)
C2 C3 C4 C5 -177.06(18)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C7 -1.8(3)
C4 C5 C6 O2 -179.73(16)
C9 O2 C6 C7 92.4(2)
C9 O2 C6 C5 -89.6(2)
C5 C6 C7 C8 1.5(3)
O2 C6 C7 C8 179.42(17)
C6 C7 C8 C3 0.7(3)
C4 C3 C8 C7 -2.5(3)
C2 C3 C8 C7 176.80(18)
C6 O2 C9 O3 -8.4(3)
C6 O2 C9 C10 171.33(16)
O3 C9 C10 C11 169.93(19)
O2 C9 C10 C11 -9.8(3)
O3 C9 C10 C15 -9.9(3)
O2 C9 C10 C15 170.38(17)
C15 C10 C11 C12 -0.4(3)
C9 C10 C11 C12 179.79(19)
C10 C11 C12 C13 -0.4(3)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 -0.3(3)
C13 C14 C15 C10 -0.4(3)
C11 C10 C15 C14 0.8(3)
C9 C10 C15 C14 -179.37(19)
