#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:06:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180287 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/01/7150141.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_7150141
loop_
_publ_author_name
'Norris, Timothy'
'Colon-Cruz, Roberto'
'Ripin, David H. B.'
_publ_section_title
;
 New hydroxy-pyrazoline intermediates, subtle regio-selectivity and
 relative reaction rate variations observed during acid catalyzed and
 neutral pyrazole cyclization.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1844
_journal_page_last               1849
_journal_paper_doi               10.1039/b500413f
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C16 H11 F3 N2'
_chemical_formula_weight         288.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 107.520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4600(10)
_cell_length_b                   16.282(2)
_cell_length_c                   10.7060(10)
_cell_measurement_reflns_used    31
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      49.795
_cell_measurement_theta_min      11.783
_cell_volume                     1406.3(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'theta and 2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1570
_diffrn_reflns_theta_full        50.00
_diffrn_reflns_theta_max         50.00
_diffrn_reflns_theta_min         5.11
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0771P)²+0.0000P] where
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                978
_reflns_number_total             1449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b500413f.txt
_cod_data_source_block           f888
_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      P2(1)/n
_cod_database_code               7150141
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'
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 0.0597(4) 0.88616(18) 0.4291(3) 0.0505(8) Uani 1 1 d . . .
N2 N 0.0349(4) 0.92848(18) 0.3150(3) 0.0556(9) Uani 1 1 d . . .
C3 C -0.1159(5) 0.9062(2) 0.2446(3) 0.0557(10) Uani 1 1 d . . .
C4 C -0.1880(5) 0.8512(2) 0.3092(3) 0.0554(11) Uani 1 1 d . . .
H4A H -0.2927 0.8276 0.2781 0.080 Uiso 1 1 calc R . .
C5 C -0.0728(5) 0.8386(2) 0.4292(3) 0.0489(10) Uani 1 1 d . . .
C6 C -0.0902(4) 0.7918(2) 0.5411(3) 0.0485(10) Uani 1 1 d . . .
C7 C -0.1554(5) 0.7136(2) 0.5227(4) 0.0626(11) Uani 1 1 d . . .
H7A H -0.1827 0.6899 0.4399 0.080 Uiso 1 1 calc R . .
C8 C -0.1807(5) 0.6700(3) 0.6251(5) 0.0745(13) Uani 1 1 d . . .
H8A H -0.2253 0.6173 0.6112 0.080 Uiso 1 1 calc R . .
C9 C -0.1404(5) 0.7038(3) 0.7468(4) 0.0736(13) Uani 1 1 d . . .
H9A H -0.1564 0.6742 0.8162 0.080 Uiso 1 1 calc R . .
C10 C -0.0758(5) 0.7822(3) 0.7672(4) 0.0679(12) Uani 1 1 d . . .
H10A H -0.0489 0.8053 0.8503 0.080 Uiso 1 1 calc R . .
C11 C -0.0511(5) 0.8261(2) 0.6652(4) 0.0580(11) Uani 1 1 d . . .
H11A H -0.0080 0.8790 0.6795 0.080 Uiso 1 1 calc R . .
C12 C -0.1874(8) 0.9416(4) 0.1117(5) 0.0784(14) Uani 1 1 d . . .
F13 F -0.3471(11) 0.9336(13) 0.0693(12) 0.138(8) Uani 0.66(3) 1 d P . .
F14 F -0.158(2) 1.0199(5) 0.1059(8) 0.117(5) Uani 0.66(3) 1 d P . .
F15 F -0.1248(18) 0.9064(9) 0.0274(7) 0.122(6) Uani 0.66(3) 1 d P . .
F13A F -0.287(8) 0.893(2) 0.037(3) 0.24(2) Uani 0.34(3) 1 d P . .
F14A F -0.276(7) 1.005(3) 0.110(2) 0.170(18) Uani 0.34(3) 1 d P . .
F15A F -0.086(3) 0.967(4) 0.055(4) 0.22(2) Uani 0.34(3) 1 d P . .
C16 C 0.2199(5) 0.8910(2) 0.5256(3) 0.0518(10) Uani 1 1 d . . .
C17 C 0.3013(5) 0.8208(3) 0.5804(4) 0.0680(12) Uani 1 1 d . . .
H17A H 0.2522 0.7697 0.5576 0.080 Uiso 1 1 calc R . .
C18 C 0.4569(6) 0.8272(4) 0.6695(5) 0.0901(16) Uani 1 1 d . . .
H18A H 0.5131 0.7800 0.7078 0.080 Uiso 1 1 calc R . .
C19 C 0.5289(6) 0.9022(4) 0.7019(5) 0.0981(17) Uani 1 1 d . . .
H19A H 0.6337 0.9062 0.7626 0.080 Uiso 1 1 calc R . .
C20 C 0.4475(7) 0.9710(3) 0.6456(5) 0.0994(17) Uani 1 1 d . . .
H20A H 0.4973 1.0221 0.6674 0.080 Uiso 1 1 calc R . .
C21 C 0.2917(5) 0.9658(3) 0.5563(4) 0.0757(13) Uani 1 1 d . . .
H21A H 0.2365 1.0130 0.5175 0.080 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C5 N1 N2 112.5(3) . . ?
C5 N1 C16 129.0(3) . . ?
N2 N1 C16 118.3(3) . . ?
C3 N2 N1 103.6(3) . . ?
N2 C3 C4 112.8(3) . . ?
N2 C3 C12 119.0(4) . . ?
C4 C3 C12 128.1(4) . . ?
C5 C4 C3 105.6(3) . . ?
N1 C5 C4 105.5(3) . . ?
N1 C5 C6 125.5(3) . . ?
C4 C5 C6 128.7(4) . . ?
C7 C6 C11 118.6(3) . . ?
C7 C6 C5 119.9(3) . . ?
C11 C6 C5 121.4(3) . . ?
C8 C7 C6 121.0(4) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 C10 120.0(4) . . ?
C11 C10 C9 120.3(4) . . ?
C10 C11 C6 120.2(4) . . ?
F13 C12 F15A 130.7(16) . . ?
F13 C12 F14A 62(2) . . ?
F15A C12 F14A 102.0(16) . . ?
F13 C12 F13A 44(3) . . ?
F15A C12 F13A 109(2) . . ?
F14A C12 F13A 103(2) . . ?
F13 C12 F15 108.1(9) . . ?
F15A C12 F15 48(3) . . ?
F14A C12 F15 134.7(9) . . ?
F13A C12 F15 67(3) . . ?
F13 C12 F14 105.9(9) . . ?
F15A C12 F14 60(2) . . ?
F14A C12 F14 47(2) . . ?
F13A C12 F14 133.4(13) . . ?
F15 C12 F14 105.9(8) . . ?
F13 C12 C3 112.2(7) . . ?
F15A C12 C3 116.7(12) . . ?
F14A C12 C3 113.4(10) . . ?
F13A C12 C3 111.7(12) . . ?
F15 C12 C3 111.0(6) . . ?
F14 C12 C3 113.4(5) . . ?
F13A F13 C12 66(2) . . ?
F13A F13 F14A 119(3) . . ?
C12 F13 F14A 58.2(12) . . ?
F14A F14 C12 64.9(16) . . ?
F14A F14 F15A 117(2) . . ?
C12 F14 F15A 58.5(15) . . ?
F15A F15 C12 63.5(19) . . ?
F15A F15 F13A 111(2) . . ?
C12 F15 F13A 54.5(16) . . ?
F13 F13A C12 70(2) . . ?
F13 F13A F15 123(3) . . ?
C12 F13A F15 58(2) . . ?
F14 F14A C12 67.9(18) . . ?
F14 F14A F13 122(2) . . ?
C12 F14A F13 59.7(16) . . ?
F15 F15A C12 68(2) . . ?
F15 F15A F14 127(3) . . ?
C12 F15A F14 61.9(17) . . ?
C21 C16 C17 120.9(4) . . ?
C21 C16 N1 118.7(4) . . ?
C17 C16 N1 120.3(4) . . ?
C16 C17 C18 119.1(4) . . ?
C19 C18 C17 120.3(5) . . ?
C20 C19 C18 119.9(5) . . ?
C19 C20 C21 120.6(5) . . ?
C16 C21 C20 119.2(4) . . ?
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
N1 C5 1.362(4) . ?
N1 N2 1.363(4) . ?
N1 C16 1.438(4) . ?
N2 C3 1.322(4) . ?
C3 C4 1.381(5) . ?
C3 C12 1.484(6) . ?
C4 C5 1.374(5) . ?
C5 C6 1.465(5) . ?
C6 C7 1.378(5) . ?
C6 C11 1.386(5) . ?
C7 C8 1.376(5) . ?
C8 C9 1.360(6) . ?
C9 C10 1.379(6) . ?
C10 C11 1.372(5) . ?
C12 F13 1.296(11) . ?
C12 F15A 1.26(2) . ?
C12 F14A 1.27(2) . ?
C12 F13A 1.26(2) . ?
C12 F15 1.309(11) . ?
C12 F14 1.304(10) . ?
F13 F13A 0.96(6) . ?
F13 F14A 1.33(4) . ?
F14 F14A 1.03(4) . ?
F14 F15A 1.27(5) . ?
F15 F15A 1.05(6) . ?
F15 F13A 1.42(6) . ?
C16 C21 1.356(5) . ?
C16 C17 1.372(5) . ?
C17 C18 1.378(6) . ?
C18 C19 1.362(7) . ?
C19 C20 1.358(7) . ?
C20 C21 1.379(6) . ?
