##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2007-09-13
_journal_date_accepted     2007-09-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     10
_journal_page_first     o4114
_journal_page_last     o4114
_journal_paper_category     QO
_journal_coeditor_code     BT2508
_publ_contact_author_name     'Professor Kari Rissanen'
_publ_contact_author_address
;
Nanoscience Center
Department of Chemistry
University of Jyvaskyla
PO Box 35
FIN-40014 University of Jyvaskyla
Finland
;
_publ_contact_author_email     kari.rissanen@jyu.fi
_publ_contact_author_fax     '+358 14 260 2651'
_publ_contact_author_phone     '+358 14 260 2672'
_publ_section_title
;
N-[1-(Silatran-1-yl)propyl]pentafluorobenzamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Lahtinen, Tanja'
;
Nanoscience Center
Department of Chemistry
University of Jyväskylä
PO Box 35
FIN-40014 Jyväskylä
Finland
;
    'Rissanen, Kari'
;
Nanoscience Center
Department of Chemistry
University of Jyväskylä
PO Box 35
FIN-40014 Jyväskylä
Finland
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
N-[3-(5-aza-2,8,9-trioxa-1-silabicyclo[3.3.3]undecan-1-yl)propyl]
pentafluorobenzamide
;
_chemical_name_common
                        'N-[1-(Silatran-1-yl)propyl]pentafluorobenzamide'
_chemical_formula_moiety     'C16 H19 F5 N2 O4 Si'
_chemical_formula_sum     'C16 H19 F5 N2 O4 Si'
_chemical_formula_iupac     'C16 H19 F5 N2 O4 Si'
_chemical_formula_weight     426.42
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     15.2027(4)
_cell_length_b     7.6207(2)
_cell_length_c     16.2411(4)
_cell_angle_alpha     90
_cell_angle_beta     110.5680(10)
_cell_angle_gamma     90
_cell_volume     1761.67(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     15147
_cell_measurement_theta_min     2.546
_cell_measurement_theta_max     27.103
_cell_measurement_temperature     173.00(10)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.608
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     880
_exptl_absorpt_coefficient_mu     0.212
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     173.00(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD with APEXII detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     5912
_diffrn_reflns_av_R_equivalents     0.0312
_diffrn_reflns_theta_min     2.68
_diffrn_reflns_theta_max     25
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3099
_reflns_number_gt     2456
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0394
_refine_ls_wR_factor_ref     0.0922
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_restrained_S_all     1.054
_refine_ls_number_reflns     3099
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.0296P)²+1.504P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.001
_refine_diff_density_max     0.215
_refine_diff_density_min     -0.271
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    Si Si 0.0817 0.0704 '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'
    O O 0.0106 0.006 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2004)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Si Si13 0.97532(4) 0.78594(8) 0.86902(4) 0.02310(16) Uani d . 1 . .
    F F2 0.40578(10) 0.6889(2) 0.84279(11) 0.0522(4) Uani d . 1 . .
    F F3 0.27692(10) 0.4350(3) 0.82441(11) 0.0594(5) Uani d . 1 . .
    F F4 0.33118(12) 0.0976(2) 0.86283(11) 0.0614(5) Uani d . 1 . .
    F F5 0.51698(13) 0.0127(2) 0.91677(13) 0.0692(5) Uani d . 1 . .
    F F6 0.64535(10) 0.2641(2) 0.93287(12) 0.0594(5) Uani d . 1 . .
    O O8 0.65323(12) 0.6813(3) 0.96762(11) 0.0464(5) Uani d . 1 . .
    O O14 0.97348(10) 0.7809(2) 0.97124(9) 0.0269(4) Uani d . 1 . .
    O O20 1.01580(10) 0.9657(2) 0.83334(10) 0.0269(4) Uani d . 1 . .
    O O21 0.97836(10) 0.5987(2) 0.81759(10) 0.0312(4) Uani d . 1 . .
    N N9 0.61017(12) 0.6639(3) 0.81880(12) 0.0278(4) Uani d . 1 . .
    H H9 0.5708 0.6143 0.7712 0.033 Uiso calc R 1 . .
    N N17 1.12283(12) 0.7347(3) 0.93537(12) 0.0262(4) Uani d . 1 . .
    C C1 0.52963(15) 0.4837(3) 0.88953(14) 0.0309(6) Uani d . 1 . .
    C C2 0.43490(16) 0.5230(4) 0.86223(15) 0.0341(6) Uani d . 1 . .
    C C3 0.36870(16) 0.3938(4) 0.85321(16) 0.0382(6) Uani d . 1 . .
    C C4 0.39591(18) 0.2229(4) 0.87225(17) 0.0413(7) Uani d . 1 . .
    C C5 0.48958(19) 0.1797(4) 0.89961(18) 0.0427(7) Uani d . 1 . .
    C C6 0.55422(16) 0.3103(4) 0.90777(16) 0.0378(6) Uani d . 1 . .
    C C7 0.60408(16) 0.6221(3) 0.89642(15) 0.0312(6) Uani d . 1 . .
    C C10 0.67912(15) 0.7881(3) 0.80927(15) 0.0288(5) Uani d . 1 . .
    H H10A 0.679 0.8942 0.8444 0.035 Uiso calc R 1 . .
    H H10B 0.6598 0.824 0.7468 0.035 Uiso calc R 1 . .
    C C11 0.77909(14) 0.7152(3) 0.83832(15) 0.0295(5) Uani d . 1 . .
    H H11A 0.8026 0.6978 0.9028 0.035 Uiso calc R 1 . .
    H H11B 0.7778 0.5991 0.8105 0.035 Uiso calc R 1 . .
    C C12 0.84674(14) 0.8355(3) 0.81418(14) 0.0257(5) Uani d . 1 . .
    H H12A 0.8355 0.9576 0.8289 0.031 Uiso calc R 1 . .
    H H12B 0.8313 0.8298 0.7497 0.031 Uiso calc R 1 . .
    C C15 1.05262(14) 0.7340(3) 1.04586(14) 0.0282(5) Uani d . 1 . .
    H H15A 1.0516 0.6064 1.0571 0.034 Uiso calc R 1 . .
    H H15B 1.0509 0.7976 1.0984 0.034 Uiso calc R 1 . .
    C C16 1.14112(15) 0.7814(3) 1.02816(14) 0.0307(5) Uani d . 1 . .
    H H16A 1.1546 0.9083 1.0378 0.037 Uiso calc R 1 . .
    H H16B 1.1955 0.7146 1.0675 0.037 Uiso calc R 1 . .
    C C18 1.17155(16) 0.8512(3) 0.89244(16) 0.0329(6) Uani d . 1 . .
    H H18A 1.1762 0.7947 0.8392 0.04 Uiso calc R 1 . .
    H H18B 1.2357 0.8788 0.9332 0.04 Uiso calc R 1 . .
    C C19 1.11278(15) 1.0158(3) 0.86826(16) 0.0305(5) Uani d . 1 . .
    H H19A 1.1245 1.0904 0.9209 0.037 Uiso calc R 1 . .
    H H19B 1.1295 1.0835 0.8239 0.037 Uiso calc R 1 . .
    C C22 1.06325(17) 0.5059(3) 0.83005(16) 0.0354(6) Uani d . 1 . .
    H H22A 1.0898 0.5422 0.7851 0.042 Uiso calc R 1 . .
    H H22B 1.0507 0.3782 0.8239 0.042 Uiso calc R 1 . .
    C C23 1.13256(16) 0.5461(3) 0.92118(16) 0.0330(6) Uani d . 1 . .
    H H23A 1.1179 0.476 0.9661 0.04 Uiso calc R 1 . .
    H H23B 1.1974 0.5186 0.9247 0.04 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Si13 O21 . 1.6625(17) ?
    Si13 O14 . 1.6706(15) ?
    Si13 O20 . 1.6860(16) ?
    Si13 C12 . 1.880(2) ?
    Si13 N17 . 2.1551(18) ?
    F2 C2 . 1.341(3) ?
    F3 C3 . 1.344(3) ?
    F4 C4 . 1.341(3) ?
    F5 C5 . 1.338(3) ?
    F6 C6 . 1.346(3) ?
    O8 C7 . 1.221(3) ?
    O14 C15 . 1.421(2) ?
    O20 C19 . 1.433(2) ?
    O21 C22 . 1.422(3) ?
    N9 C7 . 1.335(3) ?
    N9 C10 . 1.460(3) ?
    N9 H9 . 0.88 ?
    N17 C23 . 1.472(3) ?
    N17 C16 . 1.477(3) ?
    N17 C18 . 1.478(3) ?
    C1 C6 . 1.377(4) ?
    C1 C2 . 1.383(3) ?
    C1 C7 . 1.522(3) ?
    C2 C3 . 1.378(4) ?
    C3 C4 . 1.368(4) ?
    C4 C5 . 1.374(4) ?
    C5 C6 . 1.372(4) ?
    C10 C11 . 1.529(3) ?
    C10 H10A . 0.99 ?
    C10 H10B . 0.99 ?
    C11 C12 . 1.528(3) ?
    C11 H11A . 0.99 ?
    C11 H11B . 0.99 ?
    C12 H12A . 0.99 ?
    C12 H12B . 0.99 ?
    C15 C16 . 1.515(3) ?
    C15 H15A . 0.99 ?
    C15 H15B . 0.99 ?
    C16 H16A . 0.99 ?
    C16 H16B . 0.99 ?
    C18 C19 . 1.510(3) ?
    C18 H18A . 0.99 ?
    C18 H18B . 0.99 ?
    C19 H19A . 0.99 ?
    C19 H19B . 0.99 ?
    C22 C23 . 1.516(3) ?
    C22 H22A . 0.99 ?
    C22 H22B . 0.99 ?
    C23 H23A . 0.99 ?
    C23 H23B . 0.99 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O21 Si13 O14 . . 119.51(9) ?
    O21 Si13 O20 . . 116.55(8) ?
    O14 Si13 O20 . . 119.73(8) ?
    O21 Si13 C12 . . 98.18(9) ?
    O14 Si13 C12 . . 95.62(8) ?
    O20 Si13 C12 . . 96.79(9) ?
    O21 Si13 N17 . . 83.57(8) ?
    O14 Si13 N17 . . 82.92(7) ?
    O20 Si13 N17 . . 82.97(7) ?
    C12 Si13 N17 . . 178.12(9) ?
    C15 O14 Si13 . . 123.26(13) ?
    C19 O20 Si13 . . 121.96(14) ?
    C22 O21 Si13 . . 122.63(15) ?
    C7 N9 C10 . . 123.05(19) ?
    C7 N9 H9 . . 118.5 ?
    C10 N9 H9 . . 118.5 ?
    C23 N17 C16 . . 113.68(18) ?
    C23 N17 C18 . . 114.70(18) ?
    C16 N17 C18 . . 113.02(19) ?
    C23 N17 Si13 . . 104.05(14) ?
    C16 N17 Si13 . . 104.87(13) ?
    C18 N17 Si13 . . 105.15(13) ?
    C6 C1 C2 . . 116.7(2) ?
    C6 C1 C7 . . 120.7(2) ?
    C2 C1 C7 . . 122.5(2) ?
    F2 C2 C3 . . 118.7(2) ?
    F2 C2 C1 . . 120.0(2) ?
    C3 C2 C1 . . 121.3(2) ?
    F3 C3 C4 . . 119.7(2) ?
    F3 C3 C2 . . 120.0(3) ?
    C4 C3 C2 . . 120.3(2) ?
    F4 C4 C3 . . 120.0(2) ?
    F4 C4 C5 . . 120.1(3) ?
    C3 C4 C5 . . 119.8(2) ?
    F5 C5 C6 . . 120.7(2) ?
    F5 C5 C4 . . 120.4(2) ?
    C6 C5 C4 . . 118.9(3) ?
    F6 C6 C5 . . 117.7(2) ?
    F6 C6 C1 . . 119.3(2) ?
    C5 C6 C1 . . 123.0(2) ?
    O8 C7 N9 . . 125.7(2) ?
    O8 C7 C1 . . 121.2(2) ?
    N9 C7 C1 . . 113.11(19) ?
    N9 C10 C11 . . 113.86(19) ?
    N9 C10 H10A . . 108.8 ?
    C11 C10 H10A . . 108.8 ?
    N9 C10 H10B . . 108.8 ?
    C11 C10 H10B . . 108.8 ?
    H10A C10 H10B . . 107.7 ?
    C12 C11 C10 . . 112.86(19) ?
    C12 C11 H11A . . 109 ?
    C10 C11 H11A . . 109 ?
    C12 C11 H11B . . 109 ?
    C10 C11 H11B . . 109 ?
    H11A C11 H11B . . 107.8 ?
    C11 C12 Si13 . . 116.06(15) ?
    C11 C12 H12A . . 108.3 ?
    Si13 C12 H12A . . 108.3 ?
    C11 C12 H12B . . 108.3 ?
    Si13 C12 H12B . . 108.3 ?
    H12A C12 H12B . . 107.4 ?
    O14 C15 C16 . . 108.70(17) ?
    O14 C15 H15A . . 110 ?
    C16 C15 H15A . . 110 ?
    O14 C15 H15B . . 110 ?
    C16 C15 H15B . . 110 ?
    H15A C15 H15B . . 108.3 ?
    N17 C16 C15 . . 105.95(17) ?
    N17 C16 H16A . . 110.5 ?
    C15 C16 H16A . . 110.5 ?
    N17 C16 H16B . . 110.5 ?
    C15 C16 H16B . . 110.5 ?
    H16A C16 H16B . . 108.7 ?
    N17 C18 C19 . . 105.81(17) ?
    N17 C18 H18A . . 110.6 ?
    C19 C18 H18A . . 110.6 ?
    N17 C18 H18B . . 110.6 ?
    C19 C18 H18B . . 110.6 ?
    H18A C18 H18B . . 108.7 ?
    O20 C19 C18 . . 108.34(19) ?
    O20 C19 H19A . . 110 ?
    C18 C19 H19A . . 110 ?
    O20 C19 H19B . . 110 ?
    C18 C19 H19B . . 110 ?
    H19A C19 H19B . . 108.4 ?
    O21 C22 C23 . . 108.86(19) ?
    O21 C22 H22A . . 109.9 ?
    C23 C22 H22A . . 109.9 ?
    O21 C22 H22B . . 109.9 ?
    C23 C22 H22B . . 109.9 ?
    H22A C22 H22B . . 108.3 ?
    N17 C23 C22 . . 106.05(19) ?
    N17 C23 H23A . . 110.5 ?
    C22 C23 H23A . . 110.5 ?
    N17 C23 H23B . . 110.5 ?
    C22 C23 H23B . . 110.5 ?
    H23A C23 H23B . . 108.7 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N9 H9 O20 2_646 0.88 2.08 2.955(2) 172 yes
    C15 H15B O20 3_777 0.99 2.51 3.406(3) 150 yes
    C16 H16B F6 3_767 0.99 2.43 3.101(3) 125 yes
    C18 H18B F6 3_767 0.99 2.53 3.320(3) 136 yes
    C23 H23B F3 1_655 0.99 2.43 3.229(3) 137 yes
