#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/02/4000284.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_4000284
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/cm021378u
_journal_year                    2003
_chemical_formula_sum            'C18 H35 F6 N2 P'
_chemical_formula_weight         424.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.215(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6823(3)
_cell_length_b                   9.5159(2)
_cell_length_c                   25.4086(8)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      23.26
_cell_measurement_theta_min      2.26
_cell_volume                     2334.71(11)
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6359
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.2166
_refine_ls_R_factor_gt           0.1096
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3145
_refine_ls_wR_factor_ref         0.3865
_reflns_number_gt                1403
_reflns_number_total             3357
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4000284
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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
N1 N 0.1134(7) 0.1234(6) 0.5525(3) 0.1004(18) Uani 1 1 d . . .
N2 N 0.1659(8) 0.0204(7) 0.6265(3) 0.1098(19) Uani 1 1 d . . .
C1 C 0.0798(8) 0.1067(8) 0.6003(5) 0.107(2) Uani 1 1 d . . .
H1 H 0.0047 0.1499 0.6144 0.129 Uiso 1 1 calc R . .
C2 C 0.2280(10) 0.0398(11) 0.5480(4) 0.124(3) Uani 1 1 d . . .
H2 H 0.2742 0.0292 0.5175 0.149 Uiso 1 1 calc R . .
C3 C 0.2621(9) -0.0220(8) 0.5927(4) 0.121(2) Uani 1 1 d . . .
H3 H 0.3364 -0.0825 0.6002 0.145 Uiso 1 1 calc R . .
C4 C 0.0449(9) 0.2096(8) 0.5113(3) 0.140(3) Uani 1 1 d . . .
H4A H -0.0410 0.1664 0.4989 0.210 Uiso 1 1 calc R . .
H4B H 0.1035 0.2185 0.4826 0.210 Uiso 1 1 calc R . .
H4C H 0.0268 0.3011 0.5252 0.210 Uiso 1 1 calc R . .
C5 C 0.1645(10) -0.0262(10) 0.6816(4) 0.158(3) Uani 1 1 d . . .
H5A H 0.1698 -0.1279 0.6833 0.189 Uiso 1 1 calc R . .
H5B H 0.0788 0.0029 0.6959 0.189 Uiso 1 1 calc R . .
C6 C 0.289(2) 0.038(3) 0.7145(5) 0.291(11) Uani 1 1 d . . .
H6A H 0.3429 -0.0447 0.7241 0.350 Uiso 1 1 calc R . .
H6B H 0.3384 0.0835 0.6873 0.350 Uiso 1 1 calc R . .
C7 C 0.311(2) 0.099(3) 0.7443(12) 0.389(19) Uani 1 1 d . . .
H7A H 0.2571 0.0596 0.7714 0.467 Uiso 1 1 calc R . .
H7B H 0.2658 0.1862 0.7339 0.467 Uiso 1 1 calc R . .
C8 C 0.4453(16) 0.148(2) 0.7757(8) 0.258(9) Uani 1 1 d . . .
H8A H 0.5247 0.1081 0.7599 0.309 Uiso 1 1 calc R . .
H8B H 0.4519 0.2495 0.7734 0.309 Uiso 1 1 calc R . .
C9 C 0.4491(17) 0.1107(14) 0.8261(8) 0.205(6) Uani 1 1 d . . .
H9A H 0.4474 0.0089 0.8279 0.246 Uiso 1 1 calc R . .
H9B H 0.3656 0.1449 0.8407 0.246 Uiso 1 1 calc R . .
C10 C 0.5711(17) 0.1621(16) 0.8603(6) 0.214(6) Uani 1 1 d . . .
H10A H 0.6543 0.1388 0.8431 0.257 Uiso 1 1 calc R . .
H10B H 0.5658 0.2637 0.8621 0.257 Uiso 1 1 calc R . .
C11 C 0.5859(14) 0.1094(12) 0.9125(9) 0.200(5) Uani 1 1 d . . .
H11A H 0.5899 0.0077 0.9105 0.240 Uiso 1 1 calc R . .
H11B H 0.5027 0.1333 0.9295 0.240 Uiso 1 1 calc R . .
C12 C 0.705(2) 0.1567(14) 0.9469(6) 0.208(6) Uani 1 1 d . . .
H12A H 0.7871 0.1374 0.9283 0.250 Uiso 1 1 calc R . .
H12B H 0.6981 0.2582 0.9493 0.250 Uiso 1 1 calc R . .
C13 C 0.7330(13) 0.1077(16) 0.9982(9) 0.217(6) Uani 1 1 d . . .
H13A H 0.7379 0.0061 0.9956 0.260 Uiso 1 1 calc R . .
H13B H 0.6513 0.1284 1.0167 0.260 Uiso 1 1 calc R . .
C14 C 0.847(2) 0.1488(14) 1.0321(6) 0.214(6) Uani 1 1 d . . .
H14A H 0.8400 0.2500 1.0355 0.257 Uiso 1 1 calc R . .
H14B H 0.9284 0.1316 1.0128 0.257 Uiso 1 1 calc R . .
C15 C 0.8810(17) 0.0970(15) 1.0842(11) 0.236(7) Uani 1 1 d . . .
H15A H 0.8905 -0.0039 1.0805 0.284 Uiso 1 1 calc R . .
H15B H 0.7985 0.1115 1.1030 0.284 Uiso 1 1 calc R . .
C16 C 0.998(2) 0.1411(14) 1.1212(7) 0.225(6) Uani 1 1 d . . .
H16A H 1.0807 0.1233 1.1027 0.270 Uiso 1 1 calc R . .
H16B H 0.9906 0.2425 1.1236 0.270 Uiso 1 1 calc R . .
C17 C 1.033(2) 0.095(2) 1.1747(9) 0.271(8) Uani 1 1 d . . .
H17A H 0.9539 0.1181 1.1942 0.325 Uiso 1 1 calc R . .
H17B H 1.0360 -0.0072 1.1731 0.325 Uiso 1 1 calc R . .
C18 C 1.152(3) 0.135(2) 1.2082(6) 0.307(11) Uani 1 1 d . . .
H18A H 1.2321 0.1382 1.1879 0.461 Uiso 1 1 calc R . .
H18B H 1.1677 0.0674 1.2362 0.461 Uiso 1 1 calc R . .
H18C H 1.1372 0.2259 1.2230 0.461 Uiso 1 1 calc R . .
P1 P -0.3034(2) -0.0258(2) 0.61795(8) 0.1083(10) Uani 1 1 d . . .
F1 F -0.2089(7) 0.0392(8) 0.6643(2) 0.215(3) Uani 1 1 d . . .
F2 F -0.2325(5) 0.0842(6) 0.58078(19) 0.168(2) Uani 1 1 d . . .
F3 F -0.1829(7) -0.1273(6) 0.6103(4) 0.254(4) Uani 1 1 d . . .
F4 F -0.3942(7) -0.0729(10) 0.5708(2) 0.260(4) Uani 1 1 d . . .
F5 F -0.3763(7) -0.1229(6) 0.6545(3) 0.226(3) Uani 1 1 d . . .
F6 F -0.4162(6) 0.0851(6) 0.6291(2) 0.192(2) Uani 1 1 d . . .
