#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:17:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180176 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/72/7107236.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_7107236
loop_
_publ_author_name
'Kwang-Ming Lee'
'Jack C. C. Chen'
'Hsing-Yin Chen'
'Ivan J. B. Lin'
_publ_section_title
;
 A triple helical structure supported solely by C-HO hydrogen bonding
;
_journal_name_full               Chem.Commun.
_journal_page_first              1242
_journal_paper_doi               10.1039/c1cc15656j
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C9 H10 F6 N5 O P'
_chemical_formula_sum            'C9 H10 F6 N5 O P'
_chemical_formula_weight         349.19
_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                   5.5476(8)
_cell_length_b                   11.7755(16)
_cell_length_c                   20.368(2)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.989
_cell_measurement_theta_min      10.092
_cell_volume                     1330.6(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2785
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_interval_count 97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XSCANS 2.1/SHELXTL 5.1, Bruker AXS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(14)
_refine_ls_extinction_coef       0.0088(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.2460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2111
_reflns_number_total             2346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15656j.txt
_cod_data_source_block           2
_cod_original_cell_volume        1330.5(3)
_cod_database_code               7107236
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.57031(14) 0.26092(8) 0.79349(3) 0.0485(3) Uani 1 1 d . . .
O1 O -1.3274(4) 0.29065(14) 0.55849(9) 0.0429(5) Uani 1 1 d . . .
N1 N -0.8046(4) 0.05429(16) 0.58278(10) 0.0338(5) Uani 1 1 d . . .
N2 N -0.9797(4) 0.19279(17) 0.63278(10) 0.0341(5) Uani 1 1 d . . .
N3 N -0.7439(4) -0.10807(18) 0.51960(11) 0.0402(5) Uani 1 1 d . . .
N4 N -0.3258(4) -0.01554(18) 0.46493(11) 0.0420(5) Uani 1 1 d . . .
N5 N -1.3711(6) 0.4414(2) 0.62380(14) 0.0492(6) Uani 1 1 d . . .
C1 C -0.8223(5) 0.1671(2) 0.58735(12) 0.0329(5) Uani 1 1 d . . .
C2 C -0.9609(5) 0.0069(2) 0.62791(14) 0.0434(7) Uani 1 1 d . . .
C3 C -1.0694(6) 0.0927(2) 0.65918(14) 0.0450(6) Uani 1 1 d . . .
C4 C -0.6591(5) -0.00700(19) 0.53633(11) 0.0325(5) Uani 1 1 d . . .
C5 C -0.4501(5) 0.0393(2) 0.51133(13) 0.0377(6) Uani 1 1 d . . .
C6 C -0.4113(6) -0.1170(2) 0.44694(14) 0.0443(6) Uani 1 1 d . . .
C7 C -0.6115(6) -0.1616(2) 0.47544(15) 0.0468(7) Uani 1 1 d . . .
C8 C -1.0557(5) 0.3081(2) 0.64954(12) 0.0376(6) Uani 1 1 d . . .
C9 C -1.2660(5) 0.34530(19) 0.60705(11) 0.0329(5) Uani 1 1 d . . .
F1 F -0.5508(13) 0.2230(10) 0.7180(5) 0.051(3) Uani 0.50 1 d P A 1
F6 F -0.566(3) 0.2726(14) 0.8672(8) 0.120(6) Uani 0.50 1 d P A 1
F2 F -0.335(2) 0.3373(9) 0.7883(7) 0.084(3) Uani 0.50 1 d P A 1
F3 F -0.777(3) 0.1662(8) 0.8022(6) 0.091(3) Uani 0.50 1 d P A 1
F4 F -0.3741(18) 0.1657(10) 0.8058(6) 0.111(4) Uani 0.50 1 d P A 1
F5 F -0.7603(17) 0.3503(12) 0.7755(6) 0.097(4) Uani 0.50 1 d P A 1
F6' F -0.611(3) 0.3156(12) 0.8676(8) 0.084(3) Uani 0.50 1 d P A 2
F3' F -0.830(3) 0.2147(12) 0.7944(7) 0.143(6) Uani 0.50 1 d P A 2
F2' F -0.342(3) 0.3228(16) 0.7866(8) 0.169(9) Uani 0.50 1 d P A 2
F5' F -0.687(3) 0.3751(13) 0.7701(8) 0.158(7) Uani 0.50 1 d P A 2
F4' F -0.461(3) 0.1519(8) 0.8194(7) 0.144(6) Uani 0.50 1 d P A 2
F1' F -0.546(2) 0.2336(13) 0.7179(6) 0.089(5) Uani 0.50 1 d P A 2
H3 H -1.203(6) 0.087(2) 0.6930(14) 0.049(8) Uiso 1 1 d . . .
H6 H -0.329(6) -0.146(2) 0.4153(14) 0.040(8) Uiso 1 1 d . . .
H81 H -0.925(6) 0.351(2) 0.6433(13) 0.033(7) Uiso 1 1 d . . .
H2 H -0.975(6) -0.075(3) 0.6340(15) 0.055(9) Uiso 1 1 d . . .
H52 H -1.327(7) 0.474(3) 0.6595(16) 0.054(9) Uiso 1 1 d . . .
H51 H -1.488(9) 0.469(3) 0.605(2) 0.082(14) Uiso 1 1 d . . .
H1 H -0.740(5) 0.209(2) 0.5636(12) 0.027(7) Uiso 1 1 d . . .
H82 H -1.103(5) 0.305(2) 0.6993(14) 0.036(7) Uiso 1 1 d . . .
H7 H -0.668(7) -0.218(3) 0.4639(15) 0.053(10) Uiso 1 1 d . . .
H5 H -0.384(5) 0.112(2) 0.5259(12) 0.038(7) Uiso 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
F2' P1 F6 92.1(10)
F2' P1 F4' 96.2(9)
F6 P1 F4' 74.0(8)
F2' P1 F5 103.2(10)
F6 P1 F5 100.7(7)
F4' P1 F5 160.1(8)
F2' P1 F3' 169.5(10)
F6 P1 F3' 92.0(10)
F4' P1 F3' 94.1(7)
F5 P1 F3' 66.6(7)
F2' P1 F5' 84.2(10)
F6 P1 F5' 103.3(8)
F4' P1 F5' 177.3(8)
F5 P1 F5' 19.0(10)
F3' P1 F5' 85.5(8)
F2' P1 F1' 86.2(8)
F6 P1 F1' 171.3(7)
F4' P1 F1' 97.6(7)
F5 P1 F1' 88.0(7)
F3' P1 F1' 91.1(8)
F5' P1 F1' 85.1(8)
F2' P1 F4 77.0(9)
F6 P1 F4 84.1(6)
F4' P1 F4 21.4(7)
F5 P1 F4 175.2(6)
F3' P1 F4 113.0(7)
F5' P1 F4 160.1(8)
F1' P1 F4 87.2(7)
F2' P1 F2 4.9(11)
F6 P1 F2 90.1(9)
F4' P1 F2 100.0(7)
F5 P1 F2 99.2(7)
F3' P1 F2 165.8(6)
F5' P1 F2 80.4(8)
F1' P1 F2 88.9(7)
F4 P1 F2 81.2(6)
F2' P1 F1 89.3(7)
F6 P1 F1 168.1(7)
F4' P1 F1 94.1(7)
F5 P1 F1 90.5(6)
F3' P1 F1 88.6(7)
F5' P1 F1 88.6(7)
F1' P1 F1 4.5(10)
F4 P1 F1 84.7(5)
F2 P1 F1 92.2(6)
F2' P1 F3 165.8(9)
F6 P1 F3 88.0(9)
F4' P1 F3 70.1(6)
F5 P1 F3 90.8(7)
F3' P1 F3 24.2(7)
F5' P1 F3 109.6(8)
F1' P1 F3 91.5(7)
F4 P1 F3 88.9(6)
F2 P1 F3 170.0(5)
F1 P1 F3 87.8(6)
F2' P1 F6' 90.7(8)
F6 P1 F6' 19.8(9)
F4' P1 F6' 93.8(7)
F5 P1 F6' 81.8(6)
F3' P1 F6' 89.9(9)
F5' P1 F6' 83.5(8)
F1' P1 F6' 168.4(8)
F4 P1 F6' 103.0(6)
F2 P1 F6' 87.3(8)
F1 P1 F6' 172.0(6)
F3 P1 F6' 94.2(8)
C1 N1 C2 108.1(2)
C1 N1 C4 125.9(2)
C2 N1 C4 126.0(2)
C1 N2 C3 108.5(2)
C1 N2 C8 124.9(2)
C3 N2 C8 126.5(2)
C7 N3 C4 114.0(2)
C5 N4 C6 116.3(3)
N2 C1 N1 109.1(2)
C3 C2 N1 107.1(2)
C2 C3 N2 107.2(2)
N3 C4 C5 124.0(2)
N3 C4 N1 114.9(2)
C5 C4 N1 121.1(2)
N4 C5 C4 120.3(2)
N4 C6 C7 121.2(3)
N3 C7 C6 124.1(3)
N2 C8 C9 110.9(2)
O1 C9 N5 122.4(3)
O1 C9 C8 121.4(2)
N5 C9 C8 116.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 F2' 1.466(16)
P1 F6 1.508(17)
P1 F4' 1.516(9)
P1 F5 1.534(11)
P1 F3' 1.540(13)
P1 F5' 1.566(13)
P1 F1' 1.579(12)
P1 F4 1.583(9)
P1 F2 1.588(12)
P1 F1 1.605(10)
P1 F3 1.608(12)
P1 F6' 1.656(14)
O1 C9 1.228(3)
N1 C1 1.336(3)
N1 C2 1.381(4)
N1 C4 1.438(3)
N2 C1 1.308(3)
N2 C3 1.388(3)
N2 C8 1.462(3)
N3 C7 1.321(4)
N3 C4 1.324(3)
N4 C5 1.336(3)
N4 C6 1.336(3)
N5 C9 1.318(4)
C2 C3 1.338(4)
C4 C5 1.379(4)
C6 C7 1.359(4)
C8 C9 1.517(4)
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
C1 H1 O1 0.83(3) 2.49(3) 3.162(3) 140(2) 1_655
C1 H1 O1 0.83(3) 2.53(3) 3.012(3) 118(2) 4_556
C5 H5 O1 0.98(3) 2.23(3) 3.186(3) 166(2) 1_655
N5 H51 N4 0.82(5) 2.42(5) 3.223(4) 167(4) 4_356
