#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503147.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_1503147
loop_
_publ_author_name
'Zeika, Olaf'
'Li, Yongjun'
'Jockusch, Steffen'
'Parkin, Gerard'
'Sattler, Aaron'
'Sattler, Wesley'
'Turro, Nicholas J.'
_publ_section_title
;
 Synthesis of polynitroxides based on nucleophilic aromatic substitution.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3696
_journal_page_last               3699
_journal_paper_doi               10.1021/ol101529u
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C16 H17 F4 N2 O2'
_chemical_formula_weight         345.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7868(7)
_cell_length_b                   11.3770(7)
_cell_length_c                   12.9981(8)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      32.25
_cell_measurement_theta_min      2.38
_cell_volume                     1595.15(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27359
_diffrn_reflns_theta_full        32.41
_diffrn_reflns_theta_max         32.41
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.1505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                4913
_reflns_number_total             5536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101529u_si_002.cif
_cod_data_source_block           ol1s10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.80441(7) -0.17890(7) 0.06098(6) 0.03319(17) Uani 1 1 d .
F2 F 0.78364(8) 0.05705(7) 0.04875(6) 0.03268(17) Uani 1 1 d .
F3 F 0.90251(8) 0.08984(7) 0.39648(6) 0.03374(18) Uani 1 1 d .
F4 F 0.91562(9) -0.14685(7) 0.41009(6) 0.03710(19) Uani 1 1 d .
O1 O 0.46470(8) 0.51837(7) 0.25041(7) 0.02767(18) Uani 1 1 d .
O2 O 0.84421(7) 0.19750(6) 0.21356(7) 0.02411(17) Uani 1 1 d .
N1 N 0.55598(9) 0.44593(7) 0.24178(7) 0.01921(16) Uani 1 1 d .
N2 N 0.85967(12) -0.39356(9) 0.24941(13) 0.0443(3) Uani 1 1 d .
C1 C 0.85998(10) -0.16763(9) 0.23613(9) 0.0216(2) Uani 1 1 d .
C2 C 0.82789(10) -0.11319(10) 0.14397(9) 0.0212(2) Uani 1 1 d .
C3 C 0.81869(10) 0.00753(10) 0.13746(8) 0.0207(2) Uani 1 1 d .
C4 C 0.84479(9) 0.07853(9) 0.22182(8) 0.01880(19) Uani 1 1 d .
C5 C 0.87729(10) 0.02428(9) 0.31368(8) 0.0212(2) Uani 1 1 d .
C6 C 0.88486(11) -0.09674(10) 0.32058(9) 0.0229(2) Uani 1 1 d .
C7 C 0.86177(11) -0.29368(10) 0.24393(11) 0.0291(2) Uani 1 1 d .
C11 C 0.57390(10) 0.39366(9) 0.13731(8) 0.01959(19) Uani 1 1 d .
C12 C 0.70028(10) 0.33149(9) 0.13208(9) 0.0216(2) Uani 1 1 d .
H12A H 0.7046 0.2839 0.0684 0.026 Uiso 1 1 calc R
H12B H 0.7669 0.3912 0.1290 0.026 Uiso 1 1 calc R
C13 C 0.72126(9) 0.25252(9) 0.22440(8) 0.01916(19) Uani 1 1 d .
H13A H 0.6552 0.1910 0.2284 0.023 Uiso 1 1 calc R
C14 C 0.72227(10) 0.32599(9) 0.32140(8) 0.02096(19) Uani 1 1 d .
H14A H 0.7894 0.3851 0.3165 0.025 Uiso 1 1 calc R
H14B H 0.7404 0.2746 0.3810 0.025 Uiso 1 1 calc R
C15 C 0.59837(10) 0.38921(9) 0.33961(8) 0.01951(19) Uani 1 1 d .
C16 C 0.57115(12) 0.49423(10) 0.05898(9) 0.0257(2) Uani 1 1 d .
H16A H 0.6350 0.5521 0.0765 0.039 Uiso 1 1 calc R
H16B H 0.4895 0.5320 0.0603 0.039 Uiso 1 1 calc R
H16C H 0.5872 0.4629 -0.0100 0.039 Uiso 1 1 calc R
C17 C 0.46658(11) 0.30819(10) 0.11458(10) 0.0261(2) Uani 1 1 d .
H17A H 0.3875 0.3466 0.1301 0.039 Uiso 1 1 calc R
H17B H 0.4755 0.2378 0.1574 0.039 Uiso 1 1 calc R
H17C H 0.4685 0.2857 0.0418 0.039 Uiso 1 1 calc R
C18 C 0.61575(12) 0.48604(10) 0.41984(9) 0.0264(2) Uani 1 1 d .
H18A H 0.5361 0.5247 0.4328 0.040 Uiso 1 1 calc R
H18B H 0.6755 0.5439 0.3942 0.040 Uiso 1 1 calc R
H18C H 0.6468 0.4515 0.4839 0.040 Uiso 1 1 calc R
C19 C 0.49810(11) 0.30313(10) 0.37668(10) 0.0253(2) Uani 1 1 d .
H19A H 0.4183 0.3440 0.3809 0.038 Uiso 1 1 calc R
H19B H 0.5206 0.2728 0.4447 0.038 Uiso 1 1 calc R
H19C H 0.4915 0.2377 0.3280 0.038 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
C4 O2 C13 114.84(8)
O1 N1 C11 115.61(8)
O1 N1 C15 115.77(8)
C11 N1 C15 124.09(8)
C6 C1 C2 118.03(9)
C6 C1 C7 121.40(11)
C2 C1 C7 120.51(11)
F1 C2 C3 119.58(10)
F1 C2 C1 119.52(10)
C3 C2 C1 120.90(10)
F2 C3 C2 119.50(10)
F2 C3 C4 119.48(10)
C2 C3 C4 121.02(10)
O2 C4 C5 120.80(10)
O2 C4 C3 121.05(10)
C5 C4 C3 118.08(9)
F3 C5 C6 119.43(10)
F3 C5 C4 119.69(9)
C6 C5 C4 120.88(10)
F4 C6 C5 119.71(10)
F4 C6 C1 119.22(10)
C5 C6 C1 121.06(10)
N2 C7 C1 178.04(15)
N1 C11 C16 107.70(8)
N1 C11 C12 109.74(9)
C16 C11 C12 109.36(9)
N1 C11 C17 109.15(9)
C16 C11 C17 109.24(9)
C12 C11 C17 111.56(9)
C13 C12 C11 111.72(9)
O2 C13 C14 107.94(8)
O2 C13 C12 108.09(8)
C14 C13 C12 109.47(8)
C13 C14 C15 112.39(9)
N1 C15 C18 107.83(8)
N1 C15 C14 109.67(8)
C18 C15 C14 109.62(9)
N1 C15 C19 109.03(9)
C18 C15 C19 109.38(9)
C14 C15 C19 111.24(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.3366(12)
F2 C3 1.3378(12)
F3 C5 1.3373(13)
F4 C6 1.3375(13)
O1 N1 1.2889(11)
O2 C4 1.3577(12)
O2 C13 1.4733(12)
N1 C11 1.4949(14)
N1 C15 1.4975(13)
N2 C7 1.1388(16)
C1 C6 1.3883(16)
C1 C2 1.3922(16)
C1 C7 1.4377(14)
C2 C3 1.3796(15)
C3 C4 1.3908(15)
C4 C5 1.3891(15)
C5 C6 1.3822(15)
C11 C16 1.5319(15)
C11 C12 1.5373(15)
C11 C17 1.5404(16)
C12 C13 1.5160(14)
C13 C14 1.5127(15)
C14 C15 1.5361(15)
C15 C18 1.5285(15)
C15 C19 1.5366(15)
