#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:13:34 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180495 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/64/7216452.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_7216452
loop_
_publ_author_name
'Davey, Roger J.'
'Sadiq, Ghazala'
'Seaton, Colin C.'
'Pritchard, Robin G.'
'Coquerel, Gerard'
'Rougeot, Celine'
_publ_section_title
;
 Racemic compound versus conglomerate: concerning the crystal chemistry of
 the triazoylketone,
 1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-one
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              4377
_journal_paper_doi               10.1039/c4ce00615a
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H18 Cl1 N3 O1'
_chemical_formula_sum            'C15 H18 Cl N3 O'
_chemical_formula_weight         291.77
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-07-05T00:28:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7765(6)
_cell_length_b                   13.4566(13)
_cell_length_c                   19.456(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     1512.4(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.1
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3382
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3.2
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(12)
_refine_ls_extinction_coef       0.0064(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0158P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                1839
_reflns_number_total             2569
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce00615a1.cif
_cod_data_source_block           argp27
_cod_original_cell_volume        1512.3(3)
_cod_database_code               7216452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.6755(8) 0.4059(3) 0.51111(17) 0.0272(10) Uani 1 1 d
C2 C 0.4693(8) 0.4488(3) 0.5286(2) 0.0331(11) Uani 1 1 d
C3 C 0.3352(9) 0.4055(3) 0.58069(19) 0.0287(10) Uani 1 1 d
C4 C 0.4114(7) 0.3192(3) 0.61434(17) 0.0223(9) Uani 1 1 d
C5 C 0.6240(8) 0.2789(3) 0.59512(18) 0.0262(10) Uani 1 1 d
C6 C 0.7570(8) 0.3211(3) 0.54374(19) 0.0275(10) Uani 1 1 d
C7 C 0.2630(8) 0.2730(3) 0.6691(2) 0.0236(10) Uani 1 1 d
C8 C 0.3561(7) 0.2911(2) 0.74163(17) 0.0189(8) Uani 1 1 d
C9 C 0.1857(8) 0.2524(3) 0.79694(19) 0.0234(9) Uani 1 1 d
C10 C 0.2625(7) 0.2402(3) 0.87207(19) 0.0246(10) Uani 1 1 d
C11 C 0.1507(10) 0.1475(4) 0.9005(2) 0.0390(12) Uani 1 1 d
C12 C 0.1731(10) 0.3317(4) 0.9107(2) 0.0383(12) Uani 1 1 d
C13 C 0.5243(8) 0.2332(5) 0.8795(2) 0.0372(13) Uani 1 1 d
C14 C 0.2941(9) 0.5459(3) 0.7647(2) 0.0367(12) Uani 1 1 d
C15 C 0.5792(8) 0.4528(3) 0.7571(2) 0.0288(10) Uani 1 1 d
Cl1 Cl 0.8424(2) 0.45970(8) 0.44601(5) 0.0431(4) Uani 1 1 d
N1 N 0.3876(6) 0.3980(2) 0.75414(14) 0.0214(8) Uani 1 1 d
N2 N 0.1959(6) 0.4575(2) 0.75834(15) 0.0295(8) Uani 1 1 d
N3 N 0.5288(7) 0.5487(2) 0.76362(18) 0.0376(10) Uani 1 1 d
O1 O -0.0127(5) 0.2363(2) 0.78012(12) 0.0297(7) Uani 1 1 d
H8 H 0.512(7) 0.261(3) 0.7488(17) 0.036 Uiso 1 1 d
H2 H 0.423(7) 0.508(2) 0.5072(15) 0.028(11) Uiso 1 1 d
H3 H 0.193(7) 0.434(2) 0.5933(15) 0.018(10) Uiso 1 1 d
H5 H 0.667(6) 0.210(2) 0.6156(14) 0.016(9) Uiso 1 1 d
H6 H 0.907(7) 0.292(2) 0.5318(16) 0.030(11) Uiso 1 1 d
H7A H 0.250(6) 0.200(2) 0.6628(16) 0.023(10) Uiso 1 1 d
H7B H 0.110(7) 0.296(3) 0.6671(16) 0.024(11) Uiso 1 1 d
H11A H 0.204(7) 0.131(3) 0.9518(19) 0.044(12) Uiso 1 1 d
H11B H -0.015(8) 0.152(3) 0.8968(19) 0.045(14) Uiso 1 1 d
H11C H 0.205(8) 0.088(3) 0.8735(18) 0.052(15) Uiso 1 1 d
H12A H 0.246(8) 0.391(3) 0.8938(19) 0.051(14) Uiso 1 1 d
H12B H 0.211(8) 0.321(3) 0.963(2) 0.069(15) Uiso 1 1 d
H12C H -0.001(8) 0.334(3) 0.9105(18) 0.044(13) Uiso 1 1 d
H13A H 0.568(6) 0.224(3) 0.9257(17) 0.029(11) Uiso 1 1 d
H13B H 0.618(9) 0.180(3) 0.8518(19) 0.059(15) Uiso 1 1 d
H13C H 0.603(8) 0.292(3) 0.8646(17) 0.038(13) Uiso 1 1 d
H14 H 0.204(8) 0.598(3) 0.7662(18) 0.036(13) Uiso 1 1 d
H15 H 0.730(7) 0.429(3) 0.7520(17) 0.027(12) Uiso 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'
Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C2 C1 C6 121.9(4)
C2 C1 Cl1 119.1(3)
C6 C1 Cl1 119.0(4)
C1 C2 C3 119.1(4)
C2 C3 C4 120.5(4)
C5 C4 C3 118.2(4)
C5 C4 C7 122.2(3)
C3 C4 C7 119.6(4)
C6 C5 C4 121.6(4)
C5 C6 C1 118.6(4)
C4 C7 C8 112.8(3)
N1 C8 C7 110.6(3)
N1 C8 C9 107.0(3)
C7 C8 C9 111.3(3)
O1 C9 C10 120.7(3)
O1 C9 C8 118.3(4)
C10 C9 C8 120.9(4)
C11 C10 C13 109.8(4)
C11 C10 C12 109.8(4)
C13 C10 C12 109.8(4)
C11 C10 C9 108.3(3)
C13 C10 C9 112.6(3)
C12 C10 C9 106.5(3)
N2 C14 N3 116.8(4)
N3 C15 N1 111.1(4)
C15 N1 N2 110.2(3)
C15 N1 C8 130.7(4)
N2 N1 C8 118.8(3)
C14 N2 N1 100.7(4)
C15 N3 C14 101.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.367(6)
C1 C6 1.388(5)
C1 Cl1 1.749(4)
C2 C3 1.402(6)
C3 C4 1.405(5)
C4 C5 1.393(6)
C4 C7 1.502(5)
C5 C6 1.382(5)
C7 C8 1.529(5)
C8 N1 1.469(4)
C8 C9 1.549(5)
C9 O1 1.212(5)
C9 C10 1.536(5)
C10 C11 1.510(6)
C10 C13 1.522(6)
C10 C12 1.532(6)
C14 N2 1.324(5)
C14 N3 1.357(6)
C15 N3 1.328(5)
C15 N1 1.331(5)
N1 N2 1.369(4)
