#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/42/7154242.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_7154242
loop_
_publ_author_name
'Kumar, Rakesh'
'Singh, Govindra'
'Todaro, Louis J.'
'Yang, Lijia'
'Zajc, Barbara'
_publ_section_title
;
 E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with
 fluorinated second-generation Julia-Kocienski reagents.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1536
_journal_page_last               1549
_journal_paper_doi               10.1039/c4ob02179g
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C20 H20 F N3'
_chemical_formula_weight         321.39
_chemical_name_systematic
(Z)-4-(1-Fluoro-2-phenylprop-1-en-1-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 101.41(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.306(4)
_cell_length_b                   5.6030(11)
_cell_length_c                   16.578(3)
_cell_measurement_reflns_used    3804
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.95
_cell_volume                     1666.8(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'ω 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  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5987
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Slow evaporation of a solution in methylene chloride'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0043(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                2290
_reflns_number_total             3804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02179g2.cif
_cod_data_source_block           x1747l
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7154242.cif.
;
_cod_original_sg_symbol_Hall     -P2yc
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               7154242
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
F F 0.28638(7) 0.3786(2) 0.16325(6) 0.0285(3) Uani 1 1 d .
N1 N 0.22856(9) 0.4210(3) -0.08763(9) 0.0219(4) Uani 1 1 d .
N2 N 0.23917(10) 0.6587(3) -0.09231(10) 0.0267(4) Uani 1 1 d .
N3 N 0.27204(10) 0.7311(3) -0.01837(10) 0.0258(4) Uani 1 1 d .
C4 C 0.28228(11) 0.5376(3) 0.03296(12) 0.0216(5) Uani 1 1 d .
C5 C 0.25386(11) 0.3408(4) -0.01124(11) 0.0217(5) Uani 1 1 d .
H5A H 0.2524 0.1816 0.0081 0.026 Uiso 1 1 calc R
C6 C 0.31545(12) 0.5556(4) 0.12079(12) 0.0227(5) Uani 1 1 d .
C7 C 0.36379(11) 0.7068(4) 0.16268(11) 0.0221(5) Uani 1 1 d .
C8 C 0.19121(12) 0.2910(4) -0.16115(11) 0.0251(5) Uani 1 1 d .
H8A H 0.2120 0.1276 -0.1599 0.030 Uiso 1 1 calc R
H8B H 0.2015 0.3722 -0.2108 0.030 Uiso 1 1 calc R
C9 C 0.10710(12) 0.2759(4) -0.16699(12) 0.0264(5) Uani 1 1 d .
H9A H 0.0834 0.2250 -0.2233 0.032 Uiso 1 1 calc R
H9B H 0.0879 0.4367 -0.1578 0.032 Uiso 1 1 calc R
C10 C 0.08453(12) 0.1023(4) -0.10505(13) 0.0320(6) Uani 1 1 d .
H10A H 0.1058 -0.0568 -0.1124 0.038 Uiso 1 1 calc R
H10B H 0.1060 0.1577 -0.0486 0.038 Uiso 1 1 calc R
C11 C 0.00099(12) 0.0795(4) -0.11416(11) 0.0255(5) Uani 1 1 d .
C12 C -0.04002(13) 0.2607(4) -0.08700(12) 0.0300(6) Uani 1 1 d .
H12A H -0.0149 0.3981 -0.0618 0.036 Uiso 1 1 calc R
C13 C -0.11681(14) 0.2455(4) -0.09586(13) 0.0346(6) Uani 1 1 d .
H13A H -0.1437 0.3712 -0.0765 0.041 Uiso 1 1 calc R
C14 C -0.15411(13) 0.0484(4) -0.13263(13) 0.0326(6) Uani 1 1 d .
H14A H -0.2067 0.0375 -0.1389 0.039 Uiso 1 1 calc R
C15 C -0.11481(14) -0.1320(4) -0.16007(14) 0.0369(6) Uani 1 1 d .
H15A H -0.1404 -0.2685 -0.1854 0.044 Uiso 1 1 calc R
C16 C -0.03775(14) -0.1169(4) -0.15108(14) 0.0345(6) Uani 1 1 d .
H16A H -0.0113 -0.2433 -0.1706 0.041 Uiso 1 1 calc R
C17 C 0.40084(13) 0.9015(4) 0.12244(12) 0.0283(5) Uani 1 1 d .
H17A H 0.3903 0.8778 0.0627 0.042 Uiso 1 1 calc R
H17B H 0.4548 0.8962 0.1432 0.042 Uiso 1 1 calc R
H17C H 0.3815 1.0571 0.1353 0.042 Uiso 1 1 calc R
C21 C 0.38418(11) 0.6915(4) 0.25449(12) 0.0233(5) Uani 1 1 d .
C22 C 0.36684(12) 0.8809(4) 0.30216(11) 0.0258(5) Uani 1 1 d .
H22A H 0.3430 1.0192 0.2762 0.031 Uiso 1 1 calc R
C23 C 0.38436(12) 0.8677(4) 0.38712(12) 0.0308(6) Uani 1 1 d .
H23A H 0.3720 0.9965 0.4192 0.037 Uiso 1 1 calc R
C24 C 0.41966(12) 0.6686(4) 0.42553(13) 0.0329(6) Uani 1 1 d .
H24A H 0.4318 0.6606 0.4839 0.039 Uiso 1 1 calc R
C25 C 0.43739(13) 0.4808(4) 0.37875(13) 0.0345(6) Uani 1 1 d .
H25A H 0.4617 0.3436 0.4051 0.041 Uiso 1 1 calc R
C26 C 0.41987(12) 0.4922(4) 0.29369(12) 0.0298(6) Uani 1 1 d .
H26A H 0.4323 0.3628 0.2619 0.036 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'
N N 0.0061 0.0033 '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
C5 N1 N2 111.07(16)
C5 N1 C8 129.54(17)
N2 N1 C8 119.36(16)
N3 N2 N1 107.11(15)
N2 N3 C4 108.41(16)
N3 C4 C5 108.35(16)
N3 C4 C6 122.82(17)
C5 C4 C6 128.77(18)
N1 C5 C4 105.05(17)
C7 C6 F 118.59(17)
C7 C6 C4 132.08(18)
F C6 C4 109.31(16)
C6 C7 C21 120.35(18)
C6 C7 C17 123.04(18)
C21 C7 C17 116.61(17)
N1 C8 C9 112.26(16)
C8 C9 C10 113.33(17)
C11 C10 C9 112.89(17)
C16 C11 C12 117.5(2)
C16 C11 C10 122.1(2)
C12 C11 C10 120.41(19)
C13 C12 C11 121.5(2)
C14 C13 C12 120.0(2)
C15 C14 C13 119.5(2)
C14 C15 C16 120.5(2)
C11 C16 C15 121.0(2)
C26 C21 C22 119.00(18)
C26 C21 C7 121.44(18)
C22 C21 C7 119.56(18)
C23 C22 C21 120.2(2)
C24 C23 C22 120.4(2)
C23 C24 C25 119.8(2)
C24 C25 C26 120.2(2)
C25 C26 C21 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C6 1.382(2)
N1 C5 1.337(2)
N1 N2 1.350(2)
N1 C8 1.468(2)
N2 N3 1.318(2)
N3 C4 1.368(2)
C4 C5 1.369(3)
C4 C6 1.466(3)
C6 C7 1.319(3)
C7 C21 1.496(3)
C7 C17 1.508(3)
C8 C9 1.526(3)
C9 C10 1.529(3)
C10 C11 1.512(3)
C11 C16 1.384(3)
C11 C12 1.390(3)
C12 C13 1.387(3)
C13 C14 1.376(3)
C14 C15 1.370(3)
C15 C16 1.391(3)
C21 C26 1.389(3)
C21 C22 1.396(3)
C22 C23 1.383(3)
C23 C24 1.380(3)
C24 C25 1.383(3)
C25 C26 1.384(3)
