#------------------------------------------------------------------------------
#$Date: 2020-11-05 10:56:28 +0200 (Thu, 05 Nov 2020) $
#$Revision: 258736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023897.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_4023897
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                 96.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.322(17)
_cell_length_b                   15.80(2)
_cell_length_c                   8.821(12)
_cell_measurement_temperature    108(2)
_cell_volume                     1568(4)
_computing_cell_refinement       Crystallclear
_computing_data_collection       Crystallclear
_computing_data_reduction        Crystallclear
_computing_molecular_graphics    Shelxtl
_computing_publication_material  Shelxtl
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_sigmaI/netI    0.0891
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7829
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystallclear
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0843
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1324P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2287
_refine_ls_wR_factor_ref         0.2554
_reflns_number_gt                2063
_reflns_number_total             2756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014424_si_004.cif
_cod_data_source_block           shelxl
_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 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

2020-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C64 H56 F12 N12 O8'
_cod_original_formula_weight         1349.21
_cod_original_formula_units_Z            1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023897
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
F1 F 1.1011(4) 0.3098(3) 0.4975(4) 0.1038(17) Uani 1 1 d . . .
F2 F 0.9979(3) 0.3853(2) 0.3447(7) 0.135(2) Uani 1 1 d . . .
F3 F 1.1416(4) 0.3210(3) 0.2769(4) 0.1011(16) Uani 1 1 d . . .
O1 O 0.7681(2) -0.02804(15) 0.4393(3) 0.0235(6) Uani 1 1 d . . .
O2 O 0.3961(2) -0.04938(17) 0.0865(3) 0.0276(7) Uani 1 1 d . . .
N1 N 0.7461(3) 0.03417(19) 0.2026(3) 0.0240(7) Uani 1 1 d . . .
H5 H 0.7155 0.0273 0.1072 0.029 Uiso 1 1 d R . .
N2 N 0.6130(3) -0.06598(19) 0.2635(3) 0.0225(7) Uani 1 1 d . . .
H6 H 0.5821 -0.0627 0.1676 0.027 Uiso 1 1 d R . .
N3 N 0.3728(3) -0.03450(19) 0.3383(3) 0.0232(7) Uani 1 1 d . . .
H11 H 0.3406 -0.0024 0.4041 0.028 Uiso 1 1 d R . .
C1 C 1.0502(4) 0.3141(3) 0.3552(5) 0.0343(10) Uani 1 1 d . . .
C2 C 0.9738(3) 0.2398(2) 0.3120(4) 0.0289(9) Uani 1 1 d . . .
C3 C 1.0046(3) 0.1609(2) 0.3714(4) 0.0269(9) Uani 1 1 d . . .
H1 H 1.0759 0.1543 0.4381 0.032 Uiso 1 1 calc R . .
C4 C 0.9324(3) 0.0911(3) 0.3349(4) 0.0277(9) Uani 1 1 d . . .
H2 H 0.9540 0.0370 0.3759 0.033 Uiso 1 1 calc R . .
C5 C 0.8276(3) 0.1014(2) 0.2372(4) 0.0227(8) Uani 1 1 d . . .
C6 C 0.7984(3) 0.1799(2) 0.1738(4) 0.0285(9) Uani 1 1 d . . .
H3 H 0.7278 0.1864 0.1056 0.034 Uiso 1 1 calc R . .
C7 C 0.8717(4) 0.2492(3) 0.2094(4) 0.0319(9) Uani 1 1 d . . .
H4 H 0.8523 0.3027 0.1641 0.038 Uiso 1 1 calc R . .
C8 C 0.7126(3) -0.0206(2) 0.3107(4) 0.0205(8) Uani 1 1 d . . .
C9 C 0.5574(3) -0.1189(2) 0.3661(4) 0.0203(8) Uani 1 1 d . . .
C10 C 0.6232(3) -0.1862(2) 0.4371(4) 0.0256(8) Uani 1 1 d . . .
H7 H 0.7009 -0.1976 0.4116 0.031 Uiso 1 1 calc R . .
C11 C 0.5749(4) -0.2364(2) 0.5452(4) 0.0309(9) Uani 1 1 d . . .
H8 H 0.6198 -0.2815 0.5940 0.037 Uiso 1 1 calc R . .
C12 C 0.4603(4) -0.2197(3) 0.5807(4) 0.0294(9) Uani 1 1 d . . .
H9 H 0.4272 -0.2530 0.6550 0.035 Uiso 1 1 calc R . .
C13 C 0.3952(3) -0.1550(2) 0.5082(4) 0.0254(8) Uani 1 1 d . . .
H10 H 0.3165 -0.1447 0.5315 0.031 Uiso 1 1 calc R . .
C14 C 0.4433(3) -0.1041(2) 0.4008(4) 0.0223(8) Uani 1 1 d . . .
C15 C 0.3501(3) -0.0127(2) 0.1903(4) 0.0262(9) Uani 1 1 d . . .
C16 C 0.2646(4) 0.0594(3) 0.1584(5) 0.0374(10) Uani 1 1 d . . .
H20 H 0.2456 0.0837 0.2551 0.056 Uiso 1 1 calc R . .
H21 H 0.1916 0.0388 0.1000 0.056 Uiso 1 1 calc R . .
H22 H 0.3008 0.1030 0.0994 0.056 Uiso 1 1 calc R . .
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'
F F 0.0171 0.0103 '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'
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
C8 N1 C5 123.1(3) . . ?
C8 N1 H5 118.5 . . ?
C5 N1 H5 118.4 . . ?
C8 N2 C9 121.5(3) . . ?
C8 N2 H6 119.3 . . ?
C9 N2 H6 119.2 . . ?
C15 N3 C14 127.4(3) . . ?
C15 N3 H11 116.3 . . ?
C14 N3 H11 116.3 . . ?
F2 C1 F3 106.1(4) . . ?
F2 C1 F1 105.3(4) . . ?
F3 C1 F1 102.6(4) . . ?
F2 C1 C2 115.4(4) . . ?
F3 C1 C2 113.8(4) . . ?
F1 C1 C2 112.5(3) . . ?
C3 C2 C7 119.8(4) . . ?
C3 C2 C1 120.1(4) . . ?
C7 C2 C1 120.0(4) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H1 119.6 . . ?
C4 C3 H1 119.6 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H2 120.4 . . ?
C5 C4 H2 120.4 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 N1 117.6(3) . . ?
C4 C5 N1 122.2(3) . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H3 119.8 . . ?
C7 C6 H3 119.8 . . ?
C6 C7 C2 119.6(4) . . ?
C6 C7 H4 120.2 . . ?
C2 C7 H4 120.2 . . ?
O1 C8 N2 123.2(3) . . ?
O1 C8 N1 123.0(3) . . ?
N2 C8 N1 113.8(3) . . ?
C14 C9 C10 119.5(3) . . ?
C14 C9 N2 122.1(3) . . ?
C10 C9 N2 118.4(3) . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H7 119.8 . . ?
C9 C10 H7 119.8 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H8 120.3 . . ?
C10 C11 H8 120.3 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H9 120.0 . . ?
C11 C12 H9 120.0 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H10 119.6 . . ?
C14 C13 H10 119.6 . . ?
C9 C14 C13 119.8(3) . . ?
C9 C14 N3 122.7(3) . . ?
C13 C14 N3 117.4(3) . . ?
O2 C15 N3 122.9(3) . . ?
O2 C15 C16 122.0(3) . . ?
N3 C15 C16 115.1(3) . . ?
C15 C16 H20 109.5 . . ?
C15 C16 H21 109.5 . . ?
H20 C16 H21 109.5 . . ?
C15 C16 H22 109.5 . . ?
H20 C16 H22 109.5 . . ?
H21 C16 H22 109.5 . . ?
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
F1 C1 1.323(5) . ?
F2 C1 1.270(6) . ?
F3 C1 1.311(5) . ?
O1 C8 1.239(4) . ?
O2 C15 1.246(4) . ?
N1 C8 1.372(5) . ?
N1 C5 1.418(5) . ?
N1 H5 0.8800 . ?
N2 C8 1.362(5) . ?
N2 C9 1.429(4) . ?
N2 H6 0.8800 . ?
N3 C15 1.347(5) . ?
N3 C14 1.432(5) . ?
N3 H11 0.8801 . ?
C1 C2 1.482(6) . ?
C2 C3 1.382(6) . ?
C2 C7 1.394(6) . ?
C3 C4 1.389(5) . ?
C3 H1 0.9500 . ?
C4 C5 1.395(5) . ?
C4 H2 0.9500 . ?
C5 C6 1.385(5) . ?
C6 C7 1.388(6) . ?
C6 H3 0.9500 . ?
C7 H4 0.9500 . ?
C9 C14 1.381(5) . ?
C9 C10 1.404(5) . ?
C10 C11 1.398(5) . ?
C10 H7 0.9500 . ?
C11 C12 1.393(6) . ?
C11 H8 0.9500 . ?
C12 C13 1.376(6) . ?
C12 H9 0.9500 . ?
C13 C14 1.399(5) . ?
C13 H10 0.9500 . ?
C15 C16 1.501(6) . ?
C16 H20 0.9800 . ?
C16 H21 0.9800 . ?
C16 H22 0.9800 . ?
