#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023895.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_4023895
loop_
_publ_author_name
'Cidália M. G. dos Santo'
'Thomas McCabe'
'Graeme W. Watson'
'Paul E. Kruger'
'Thorfinnur Gunnlaugsson'
_publ_section_title
;
 The Recognition and Sensing of Anions through "Positive
 Allosteric Effects" Using Simple Urea--Amide Receptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9235
_journal_page_last               9244
_journal_paper_doi               10.1021/jo8014424
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C16 H14 F3 N3 O2'
_chemical_formula_weight         337.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.585(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9903(12)
_cell_length_b                   7.6035(8)
_cell_length_c                   17.4995(18)
_cell_measurement_reflns_used    1644
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      19.71
_cell_measurement_theta_min      2.42
_cell_volume                     1536.7(3)
_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      571(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11791
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, ActaCryst. (1995) A51 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0584P)²+0.0788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                1702
_reflns_number_total             2701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014424_si_002.cif
_cod_data_source_block           cs030m
_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/c'
_cod_database_code               4023895
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O2 O 0.68790(16) -0.0091(2) 0.17175(9) 0.0582(5) Uani 1 1 d . . .
O1 O 0.31619(17) 0.8452(2) 0.08726(10) 0.0651(6) Uani 1 1 d . . .
N3 N 0.34717(18) 0.6401(3) 0.18377(11) 0.0491(6) Uani 1 1 d . . .
H3 H 0.3297 0.6099 0.2265 0.059 Uiso 1 1 calc R . .
N1 N 0.73440(19) -0.0585(3) 0.05578(11) 0.0533(6) Uani 1 1 d . . .
H1 H 0.7272 -0.0162 0.0091 0.064 Uiso 1 1 calc R . .
C14 C 0.2990(2) 0.7876(4) 0.14860(14) 0.0511(7) Uani 1 1 d . . .
F2 F 1.08767(16) -0.6864(2) 0.14716(10) 0.0833(6) Uani 1 1 d . . .
C6 C 0.7961(2) -0.2161(3) 0.07345(13) 0.0445(6) Uani 1 1 d . . .
C8 C 0.5640(2) 0.2965(3) 0.10307(13) 0.0451(6) Uani 1 1 d . . .
F3 F 0.93659(17) -0.8053(2) 0.16524(11) 0.0914(6) Uani 1 1 d . . .
C5 C 0.8047(2) -0.3193(3) 0.01028(14) 0.0530(7) Uani 1 1 d . . .
H5 H 0.7718 -0.2805 -0.0413 0.064 Uiso 1 1 calc R . .
C7 C 0.6845(2) 0.0356(4) 0.10394(14) 0.0476(7) Uani 1 1 d . . .
C10 C 0.4176(2) 0.3505(3) 0.16986(14) 0.0482(7) Uani 1 1 d . . .
H10 H 0.3664 0.3081 0.1971 0.058 Uiso 1 1 calc R . .
C12 C 0.5046(2) 0.5913(3) 0.12113(15) 0.0528(7) Uani 1 1 d . . .
H12 H 0.5122 0.7117 0.1147 0.063 Uiso 1 1 calc R . .
F1 F 0.96369(17) -0.8030(2) 0.04953(11) 0.0862(6) Uani 1 1 d . . .
N2 N 0.6298(2) 0.1827(3) 0.06891(12) 0.0584(6) Uani 1 1 d . . .
H2 H 0.6358 0.2083 0.0223 0.070 Uiso 1 1 calc R . .
C9 C 0.4857(2) 0.2341(4) 0.14227(13) 0.0486(7) Uani 1 1 d . . .
H9 H 0.4791 0.1139 0.1499 0.058 Uiso 1 1 calc R . .
C11 C 0.4241(2) 0.5281(3) 0.15788(13) 0.0428(6) Uani 1 1 d . . .
C1 C 0.9122(2) -0.5358(3) 0.09810(14) 0.0497(7) Uani 1 1 d . . .
C13 C 0.5733(2) 0.4756(4) 0.09425(15) 0.0556(7) Uani 1 1 d . . .
H13 H 0.6273 0.5190 0.0696 0.067 Uiso 1 1 calc R . .
C4 C 0.8612(2) -0.4783(4) 0.02238(15) 0.0559(7) Uani 1 1 d . . .
H4 H 0.8649 -0.5471 -0.0208 0.067 Uiso 1 1 calc R . .
C3 C 0.8483(2) -0.2722(4) 0.14955(14) 0.0568(7) Uani 1 1 d . . .
H3A H 0.8451 -0.2031 0.1927 0.068 Uiso 1 1 calc R . .
C15 C 0.2190(3) 0.8798(4) 0.18786(18) 0.0794(10) Uani 1 1 d . . .
H15A H 0.2538 0.9880 0.2108 0.119 Uiso 1 1 calc R . .
H15B H 0.2048 0.8060 0.2288 0.119 Uiso 1 1 calc R . .
H15C H 0.1471 0.9045 0.1492 0.119 Uiso 1 1 calc R . .
C2 C 0.9053(2) -0.4309(4) 0.16124(15) 0.0571(7) Uani 1 1 d . . .
H2A H 0.9399 -0.4686 0.2127 0.069 Uiso 1 1 calc R . .
C16 C 0.9733(3) -0.7048(4) 0.11376(17) 0.0633(8) 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'
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
_geom_angle_publ_flag
C14 N3 C11 126.61(19) . . ?
C7 N1 C6 127.4(2) . . ?
O1 C14 N3 123.4(2) . . ?
O1 C14 C15 120.9(2) . . ?
N3 C14 C15 115.7(2) . . ?
C3 C6 C5 119.0(2) . . ?
C3 C6 N1 123.7(2) . . ?
C5 C6 N1 117.3(2) . . ?
C13 C8 C9 118.6(2) . . ?
C13 C8 N2 119.2(2) . . ?
C9 C8 N2 122.1(2) . . ?
C4 C5 C6 121.1(2) . . ?
O2 C7 N2 123.6(2) . . ?
O2 C7 N1 123.3(2) . . ?
N2 C7 N1 113.2(2) . . ?
C11 C10 C9 121.1(2) . . ?
C13 C12 C11 119.7(2) . . ?
C7 N2 C8 124.9(2) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 N3 118.3(2) . . ?
C12 C11 N3 122.4(2) . . ?
C4 C1 C2 118.7(2) . . ?
C4 C1 C16 122.0(2) . . ?
C2 C1 C16 119.3(2) . . ?
C12 C13 C8 121.4(2) . . ?
C1 C4 C5 120.1(2) . . ?
C2 C3 C6 119.6(2) . . ?
C3 C2 C1 121.4(2) . . ?
F1 C16 F3 106.2(3) . . ?
F1 C16 F2 105.8(2) . . ?
F3 C16 F2 104.3(2) . . ?
F1 C16 C1 114.1(2) . . ?
F3 C16 C1 112.7(2) . . ?
F2 C16 C1 112.9(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.225(3) . ?
O1 C14 1.227(3) . ?
N3 C14 1.334(3) . ?
N3 C11 1.416(3) . ?
N1 C7 1.360(3) . ?
N1 C6 1.398(3) . ?
C14 C15 1.496(4) . ?
F2 C16 1.346(3) . ?
C6 C3 1.378(3) . ?
C6 C5 1.382(3) . ?
C8 C13 1.379(3) . ?
C8 C9 1.387(3) . ?
C8 N2 1.408(3) . ?
F3 C16 1.342(3) . ?
C5 C4 1.374(3) . ?
C7 N2 1.357(3) . ?
C10 C11 1.372(3) . ?
C10 C9 1.376(3) . ?
C12 C13 1.372(3) . ?
C12 C11 1.383(3) . ?
F1 C16 1.328(3) . ?
C1 C4 1.373(3) . ?
C1 C2 1.383(3) . ?
C1 C16 1.468(4) . ?
C3 C2 1.374(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658801
