#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/20/4022086.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_4022086
loop_
_publ_author_name
'Ireneusz Nowak'
'Morris J. Robins'
_publ_section_title
;
 Addition of Difluorocarbene to 4',5'-Unsaturated Nucleosides:
 Synthesis and Deoxygenation Reactions of
 Difluorospirocyclopropane Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8876
_journal_page_last               8883
_journal_paper_doi               10.1021/jo061606u
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H18 F2 N2 O6'
_chemical_formula_weight         420.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 114.245(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.0009(18)
_cell_length_b                   7.0164(10)
_cell_length_c                   12.796(2)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.65
_cell_measurement_theta_min      4.54
_cell_volume                     982.4(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'Theta/2-theta 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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3179
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.03
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9327
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0416P)²+0.0847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2150
_reflns_number_total             2430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061606usi20060803_013934.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022086
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C2 C 0.82329(17) 0.4894(3) 0.92395(16) 0.0313(4) Uani 1 1 d .
C4 C 0.8795(2) 0.2736(4) 1.09264(18) 0.0407(5) Uani 1 1 d .
C5 C 0.8619(2) 0.1179(3) 1.01541(19) 0.0446(5) Uani 1 1 d .
H5 H 0.8754 -0.0062 1.0434 0.054 Uiso 1 1 calc R
C6 C 0.82624(19) 0.1493(3) 0.90387(18) 0.0369(4) Uani 1 1 d .
H6 H 0.8141 0.0451 0.8555 0.044 Uiso 1 1 calc R
C1' C 0.76058(18) 0.3492(3) 0.73180(15) 0.0343(4) Uani 1 1 d .
H1' H 0.7623 0.2225 0.7002 0.041 Uiso 1 1 calc R
C2' C 0.83075(18) 0.4839(4) 0.68754(16) 0.0371(5) Uani 1 1 d .
H2' H 0.9070 0.5296 0.7483 0.045 Uiso 1 1 calc R
C3' C 0.74200(19) 0.6459(4) 0.62687(16) 0.0399(5) Uani 1 1 d .
H3' H 0.7756 0.7719 0.6560 0.048 Uiso 1 1 calc R
C4' C 0.62988(19) 0.5999(3) 0.64722(17) 0.0370(5) Uani 1 1 d .
C5' C 0.5663(2) 0.7411(4) 0.6878(2) 0.0472(6) Uani 1 1 d .
C6' C 0.5018(2) 0.6687(4) 0.5709(2) 0.0507(6) Uani 1 1 d .
H6'1 H 0.4926 0.7533 0.5079 0.061 Uiso 1 1 calc R
H6'2 H 0.4343 0.5814 0.5560 0.061 Uiso 1 1 calc R
C2'A C 0.8154(2) 0.5157(4) 0.50370(18) 0.0462(6) Uani 1 1 d .
C3'A C 0.9203(3) 0.6431(6) 0.5150(2) 0.0680(8) Uani 1 1 d .
H3'1 H 0.9521 0.7031 0.5889 0.102 Uiso 1 1 calc R
H3'2 H 0.8925 0.7389 0.4563 0.102 Uiso 1 1 calc R
H3'3 H 0.9834 0.5686 0.5069 0.102 Uiso 1 1 calc R
C4'A C 0.7688(3) 0.4024(6) 0.3952(2) 0.0630(8) Uani 1 1 d .
H4'1 H 0.8345 0.3294 0.3909 0.094 Uiso 1 1 calc R
H4'2 H 0.7365 0.4871 0.3307 0.094 Uiso 1 1 calc R
H4'3 H 0.7055 0.3178 0.3942 0.094 Uiso 1 1 calc R
C1B C 0.8656(2) 0.6177(3) 1.11306(16) 0.0360(4) Uani 1 1 d .
C2B C 0.75390(19) 0.6683(4) 1.12758(16) 0.0393(5) Uani 1 1 d .
C3B C 0.7596(3) 0.8246(4) 1.1955(2) 0.0536(6) Uani 1 1 d .
H3B H 0.8309 0.8962 1.2276 0.064 Uiso 1 1 calc R
C4B C 0.6578(3) 0.8735(5) 1.2152(3) 0.0737(9) Uani 1 1 d .
H4B H 0.6604 0.9791 1.2601 0.088 Uiso 1 1 calc R
C5B C 0.5534(3) 0.7662(6) 1.1687(3) 0.0794(11) Uani 1 1 d .
H5B H 0.4863 0.7979 1.1839 0.095 Uiso 1 1 calc R
C6B C 0.5466(3) 0.6135(6) 1.1002(3) 0.0720(9) Uani 1 1 d .
H6B H 0.4748 0.5430 1.0680 0.086 Uiso 1 1 calc R
C7B C 0.6475(2) 0.5636(4) 1.0786(2) 0.0520(6) Uani 1 1 d .
H7B H 0.6433 0.4603 1.0316 0.062 Uiso 1 1 calc R
F1 F 0.60602(16) 0.9234(2) 0.70342(16) 0.0669(5) Uani 1 1 d .
F2 F 0.52860(14) 0.6962(3) 0.76925(13) 0.0656(5) Uani 1 1 d .
N1 N 0.80646(16) 0.3295(3) 0.85674(13) 0.0325(4) Uani 1 1 d .
N3 N 0.85530(16) 0.4525(3) 1.03873(14) 0.0344(4) Uani 1 1 d .
O2 O 0.80971(15) 0.6496(2) 0.88629(12) 0.0413(4) Uani 1 1 d .
O4 O 0.9097(2) 0.2649(3) 1.19548(13) 0.0589(5) Uani 1 1 d .
O2' O 0.84940(15) 0.3890(3) 0.59832(13) 0.0503(4) Uani 1 1 d .
O3' O 0.71696(15) 0.6220(3) 0.50900(12) 0.0547(5) Uani 1 1 d .
O4' O 0.63726(13) 0.4109(2) 0.68606(12) 0.0393(3) Uani 1 1 d .
O1B O 0.96085(15) 0.6975(3) 1.15666(15) 0.0542(4) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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
O2 C2 N1 123.24(17)
O2 C2 N3 122.12(19)
N1 C2 N3 114.63(18)
O4 C4 N3 119.1(2)
O4 C4 C5 127.2(2)
N3 C4 C5 113.68(17)
C6 C5 C4 120.4(2)
C5 C6 N1 122.9(2)
O4' C1' N1 109.84(15)
O4' C1' C2' 107.45(17)
N1 C1' C2' 116.51(17)
O2' C2' C1' 107.59(19)
O2' C2' C3' 104.32(16)
C1' C2' C3' 105.87(17)
O3' C3' C4' 110.08(17)
O3' C3' C2' 104.48(18)
C4' C3' C2' 103.76(18)
O4' C4' C5' 118.54(19)
O4' C4' C3' 109.39(18)
C5' C4' C3' 123.1(2)
O4' C4' C6' 115.2(2)
C5' C4' C6' 58.59(16)
C3' C4' C6' 124.00(19)
F2 C5' F1 108.7(2)
F2 C5' C6' 120.6(2)
F1 C5' C6' 119.1(2)
F2 C5' C4' 120.6(2)
F1 C5' C4' 119.2(2)
C6' C5' C4' 62.50(16)
C5' C6' C4' 58.90(15)
O2' C2'A O3' 103.92(15)
O2' C2'A C4'A 109.0(3)
O3' C2'A C4'A 108.7(2)
O2' C2'A C3'A 110.8(2)
O3' C2'A C3'A 111.3(3)
C4'A C2'A C3'A 112.7(2)
O1B C1B C2B 125.4(2)
O1B C1B N3 119.0(2)
C2B C1B N3 115.62(19)
C7B C2B C3B 120.3(2)
C7B C2B C1B 122.4(2)
C3B C2B C1B 117.3(2)
C2B C3B C4B 119.4(3)
C5B C4B C3B 120.1(3)
C6B C5B C4B 120.9(3)
C5B C6B C7B 119.8(3)
C2B C7B C6B 119.6(3)
C2 N1 C6 121.28(16)
C2 N1 C1' 119.78(17)
C6 N1 C1' 118.87(17)
C2 N3 C4 126.95(18)
C2 N3 C1B 116.89(17)
C4 N3 C1B 116.16(15)
C2' O2' C2'A 107.90(19)
C3' O3' C2'A 107.14(16)
C4' O4' C1' 109.74(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O2 1.208(3)
C2 N1 1.377(3)
C2 N3 1.381(2)
C4 O4 1.214(3)
C4 N3 1.404(3)
C4 C5 1.430(3)
C5 C6 1.329(3)
C6 N1 1.379(3)
C1' O4' 1.417(2)
C1' N1 1.468(2)
C1' C2' 1.522(3)
C2' O2' 1.417(3)
C2' C3' 1.533(3)
C3' O3' 1.422(2)
C3' C4' 1.507(3)
C4' O4' 1.406(3)
C4' C5' 1.469(3)
C4' C6' 1.522(3)
C5' F2 1.334(3)
C5' F1 1.351(3)
C5' C6' 1.464(3)
C2'A O2' 1.420(3)
C2'A O3' 1.422(3)
C2'A C4'A 1.495(4)
C2'A C3'A 1.501(4)
C1B O1B 1.186(3)
C1B C2B 1.471(3)
C1B N3 1.472(3)
C2B C7B 1.380(4)
C2B C3B 1.384(3)
C3B C4B 1.388(4)
C4B C5B 1.370(5)
C5B C6B 1.365(5)
C6B C7B 1.393(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194220
