#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:48:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178445 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/66/4026609.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_4026609
loop_
_publ_author_name
'Goutam Kumar Kole'
'Geok Kheng Tan'
'Jagadese J. Vittal'
_publ_contact_author
; 
     Dr. Jagadese J. Vittal
     Department of Chemistry
     National University of Singapore
     3 Science Drive 3
     SINGAPORE 117543 
;
_publ_contact_author_email       chmjjv@nus.edu.sg
_publ_contact_author_fax         '(65) 6779 1691'
_publ_contact_author_phone       '(65) 6516 2677'
_publ_section_title
;
 Role of Anions in the Synthesis of Cyclobutane Derivatives via [2 + 2]
 Cycloaddition Reaction in the Solid State and Their Isomerization in
 Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7860
_journal_page_last               7865
_journal_paper_doi               10.1021/jo201268p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H15 F6 N2 O4 P'
_chemical_formula_weight         444.27
_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                 95.9440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0962(3)
_cell_length_b                   15.5577(10)
_cell_length_c                   11.4752(8)
_cell_measurement_reflns_used    3985
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.21
_cell_volume                     904.92(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6198
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9146
_exptl_absorpt_correction_T_min  0.9104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0464
_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)+(0.0610P)²+0.6181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                1908
_reflns_number_total             2069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201268p_si_002_4.cif
_cod_data_source_block           compound_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4026609
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.5000 0.5000 0.5000 0.0307(2) Uani 1 2 d S . .
F1 F 0.3208(3) 0.48934(8) 0.60585(12) 0.0509(4) Uani 1 1 d . A .
F2 F 0.3274(4) 0.42810(14) 0.43005(18) 0.0736(7) Uani 0.830(2) 1 d P A 1
F3 F 0.3064(4) 0.57238(14) 0.44711(19) 0.0777(7) Uani 0.830(2) 1 d P A 1
F2A F 0.503(2) 0.4003(7) 0.4842(9) 0.0736(7) Uani 0.170(2) 1 d P A 2
F3A F 0.276(2) 0.5061(7) 0.3988(10) 0.0777(7) Uani 0.170(2) 1 d P A 2
O1 O 0.8248(3) 0.47640(9) 0.92551(14) 0.0501(4) Uani 1 1 d . . .
H1O H 0.950(14) 0.489(5) 0.974(5) 0.067(19) Uiso 0.50 1 d P . .
O2 O 0.9958(3) 0.34620(8) 0.95783(12) 0.0389(3) Uani 1 1 d . . .
N1 N -0.0793(3) 0.16527(10) 0.61198(12) 0.0307(3) Uani 1 1 d . . .
H1N H -0.221(6) 0.1410(18) 0.566(2) 0.064(8) Uiso 1 1 d . . .
C1 C -0.0391(3) 0.24963(11) 0.60092(14) 0.0293(4) Uani 1 1 d . . .
H1 H -0.1544 0.2822 0.5491 0.035 Uiso 1 1 calc R . .
C2 C 0.1694(3) 0.28886(10) 0.66476(14) 0.0277(3) Uani 1 1 d . . .
H2 H 0.1977 0.3482 0.6569 0.033 Uiso 1 1 calc R . .
C3 C 0.3400(3) 0.23987(10) 0.74185(13) 0.0236(3) Uani 1 1 d . . .
C4 C 0.2913(3) 0.15224(11) 0.75029(15) 0.0331(4) Uani 1 1 d . . .
H4 H 0.4033 0.1177 0.8010 0.040 Uiso 1 1 calc R . .
C5 C 0.0782(4) 0.11619(11) 0.68414(16) 0.0376(4) Uani 1 1 d . . .
H5 H 0.0441 0.0570 0.6899 0.045 Uiso 1 1 calc R . .
C6 C 0.5638(3) 0.27790(10) 0.81518(13) 0.0249(3) Uani 1 1 d . . .
H6 H 0.6847 0.2402 0.8559 0.030 Uiso 1 1 calc R . .
C7 C 0.6074(3) 0.36107(11) 0.82798(14) 0.0298(4) Uani 1 1 d . . .
H7 H 0.4951 0.3999 0.7844 0.036 Uiso 1 1 calc R . .
C8 C 0.8294(3) 0.39515(10) 0.90949(14) 0.0276(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 0.0000 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'
P P 0.1023 0.0942 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
F3A P1 F3A 179.997(3) 3_666 .
F3A P1 F2A 89.4(6) 3_666 3_666
F3A P1 F2A 90.6(6) . 3_666
F3A P1 F2A 90.6(6) 3_666 .
F3A P1 F2A 89.4(6) . .
F2A P1 F2A 179.999(3) 3_666 .
F3A P1 F3 44.1(4) 3_666 3_666
F3A P1 F3 135.9(4) . 3_666
F2A P1 F3 132.7(4) 3_666 3_666
F2A P1 F3 47.3(4) . 3_666
F3A P1 F3 135.9(4) 3_666 .
F3A P1 F3 44.1(4) . .
F2A P1 F3 47.3(4) 3_666 .
F2A P1 F3 132.7(4) . .
F3 P1 F3 179.998(1) 3_666 .
F3A P1 F2 131.6(4) 3_666 .
F3A P1 F2 48.4(4) . .
F2A P1 F2 138.2(4) 3_666 .
F2A P1 F2 41.8(4) . .
F3 P1 F2 89.04(14) 3_666 .
F3 P1 F2 90.96(14) . .
F3A P1 F2 48.4(4) 3_666 3_666
F3A P1 F2 131.6(4) . 3_666
F2A P1 F2 41.8(4) 3_666 3_666
F2A P1 F2 138.2(4) . 3_666
F3 P1 F2 90.96(14) 3_666 3_666
F3 P1 F2 89.04(14) . 3_666
F2 P1 F2 179.998(1) . 3_666
F3A P1 F1 81.9(4) 3_666 .
F3A P1 F1 98.1(4) . .
F2A P1 F1 90.0(3) 3_666 .
F2A P1 F1 90.0(3) . .
F3 P1 F1 91.00(9) 3_666 .
F3 P1 F1 89.00(9) . .
F2 P1 F1 88.90(8) . .
F2 P1 F1 91.10(8) 3_666 .
F3A P1 F1 98.1(4) 3_666 3_666
F3A P1 F1 81.9(4) . 3_666
F2A P1 F1 90.0(3) 3_666 3_666
F2A P1 F1 90.0(3) . 3_666
F3 P1 F1 89.00(9) 3_666 3_666
F3 P1 F1 91.00(9) . 3_666
F2 P1 F1 91.09(8) . 3_666
F2 P1 F1 88.91(8) 3_666 3_666
F1 P1 F1 180.0 . 3_666
C5 N1 C1 122.22(14) . .
N1 C1 C2 120.32(15) . .
C1 C2 C3 119.47(15) . .
C4 C3 C2 118.28(14) . .
C4 C3 C6 119.24(14) . .
C2 C3 C6 122.48(14) . .
C5 C4 C3 119.79(15) . .
N1 C5 C4 119.92(16) . .
C7 C6 C3 124.80(14) . .
C6 C7 C8 121.85(15) . .
O2 C8 O1 124.77(15) . .
O2 C8 C7 120.46(15) . .
O1 C8 C7 114.74(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F3A 1.545(11) 3_666
P1 F3A 1.546(11) .
P1 F2A 1.563(11) 3_666
P1 F2A 1.563(11) .
P1 F3 1.5767(16) 3_666
P1 F3 1.5767(16) .
P1 F2 1.5884(16) .
P1 F2 1.5884(16) 3_666
P1 F1 1.6021(12) .
P1 F1 1.6021(12) 3_666
O1 C8 1.278(2) .
O2 C8 1.228(2) .
N1 C5 1.333(2) .
N1 C1 1.336(2) .
C1 C2 1.370(2) .
C2 C3 1.400(2) .
C3 C4 1.391(2) .
C3 C6 1.470(2) .
C4 C5 1.378(2) .
C6 C7 1.318(2) .
C7 C8 1.489(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O1 0.83(6) 1.63(6) 2.453(3) 173(8) 3_767
N1 H1N O2 0.93(3) 1.82(3) 2.6563(18) 149(3) 4_465
N1 H1N O1 0.93(3) 2.62(3) 3.205(2) 122(2) 2_546
