#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/97/2019745.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019745
loop_
_publ_author_name
'Bustos, Carlos'
'Alvarez-Thon, Luis'
'Oportus, Tania'
'Mesías-Salazar, Angela'
'Baggio, Ricardo'
_publ_section_title
;
 On substituted pyrazole derivatives. II.
 (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone
 and
 (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole
;
_journal_coeditor_code           YF3075
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229614024619
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C17 H14 Cl N5 O2'
_chemical_formula_moiety         'C17 H14 Cl N5 O2'
_chemical_formula_sum            'C17 H14 Cl N5 O2'
_chemical_formula_weight         355.78
_chemical_name_systematic
(E)-1-(4-Chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.076(5)
_cell_length_b                   30.549(12)
_cell_length_c                   7.539(3)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.92
_cell_volume                     3242(2)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_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  0.0855
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25152
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.902
_diffrn_reflns_theta_min         1.593
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS in SAINT; Bruker, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0487P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                2412
_reflns_number_total             3710
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3075sup1.cif
_cod_data_source_block           IV
_cod_database_code               2019745
_cod_database_fobs_code          2019745
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 0.37814(3) 0.24807(2) 0.71131(6) 0.03424(14) Uani d 1
O O1 0.50290(10) 0.64203(4) 0.75685(17) 0.0439(4) Uani d 1
O O2 0.40551(9) 0.69588(4) 0.80209(17) 0.0392(3) Uani d 1
N N1 0.36963(9) 0.44197(4) 0.68307(18) 0.0231(3) Uani d 1
N N2 0.37066(10) 0.46453(4) 0.84302(18) 0.0254(3) Uani d 1
N N3 0.38053(9) 0.54756(4) 0.49949(18) 0.0234(3) Uani d 1
N N4 0.38129(9) 0.58420(4) 0.58077(18) 0.0245(3) Uani d 1
N N5 0.43951(10) 0.66668(4) 0.70930(19) 0.0281(3) Uani d 1
C C1 0.36813(11) 0.39517(5) 0.6903(2) 0.0222(4) Uani d 1
C C2 0.41938(11) 0.37431(5) 0.8227(2) 0.0238(4) Uani d 1
H H2 0.4539 0.3911 0.9070 0.029 Uiso calc 1
C C3 0.42046(11) 0.32906(5) 0.8326(2) 0.0250(4) Uani d 1
H H3 0.4546 0.3147 0.9243 0.030 Uiso calc 1
C C4 0.37080(11) 0.30491(5) 0.7061(2) 0.0242(4) Uani d 1
C C5 0.31740(12) 0.32546(5) 0.5765(2) 0.0281(4) Uani d 1
H H5 0.2827 0.3086 0.4926 0.034 Uiso calc 1
C C6 0.31486(12) 0.37084(5) 0.5698(2) 0.0273(4) Uani d 1
H H6 0.2770 0.3852 0.4834 0.033 Uiso calc 1
C C7 0.37428(11) 0.46896(5) 0.5407(2) 0.0219(4) Uani d 1
C C8 0.37702(11) 0.51114(5) 0.6100(2) 0.0225(4) Uani d 1
C C9 0.37459(11) 0.50658(5) 0.7986(2) 0.0235(4) Uani d 1
C C10 0.37761(11) 0.62078(5) 0.4626(2) 0.0222(4) Uani d 1
C C11 0.33988(11) 0.61869(5) 0.2919(2) 0.0256(4) Uani d 1
H H11 0.3221 0.5912 0.2436 0.031 Uiso calc 1
C C12 0.32817(12) 0.65619(5) 0.1925(2) 0.0290(4) Uani d 1
H H12 0.3035 0.6541 0.0754 0.035 Uiso calc 1
C C13 0.35197(12) 0.69700(6) 0.2614(2) 0.0310(4) Uani d 1
H H13 0.3431 0.7226 0.1920 0.037 Uiso calc 1
C C14 0.38828(11) 0.70013(5) 0.4302(2) 0.0280(4) Uani d 1
H H14 0.4043 0.7278 0.4790 0.034 Uiso calc 1
C C15 0.40113(12) 0.66209(5) 0.5281(2) 0.0239(4) Uani d 1
C C16 0.37713(13) 0.54081(5) 0.9409(2) 0.0313(4) Uani d 1
H H16A 0.3698 0.5268 1.0571 0.047 Uiso calc 1
H H16B 0.3252 0.5617 0.9222 0.047 Uiso calc 1
H H16C 0.4380 0.5563 0.9364 0.047 Uiso calc 1
C C17 0.38089(12) 0.45477(5) 0.3520(2) 0.0257(4) Uani d 1
H H17A 0.4168 0.4273 0.3448 0.039 Uiso calc 1
H H17B 0.4134 0.4774 0.2826 0.039 Uiso calc 1
H H17C 0.3169 0.4502 0.3043 0.039 Uiso calc 1
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'
Cl Cl 0.1484 0.1585 '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
C7 N1 N2 112.66(13)
C7 N1 C1 129.71(13)
N2 N1 C1 117.56(12)
C9 N2 N1 105.15(13)
N4 N3 C8 114.47(14)
N3 N4 C10 112.72(14)
O1 N5 O2 124.35(15)
O1 N5 C15 118.73(13)
O2 N5 C15 116.92(14)
C2 C1 C6 120.28(15)
C2 C1 N1 118.64(14)
C6 C1 N1 121.07(14)
C3 C2 C1 120.23(15)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 119.11(15)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 121.03(15)
C5 C4 Cl1 120.06(13)
C3 C4 Cl1 118.90(13)
C4 C5 C6 119.53(15)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C1 119.70(16)
C5 C6 H6 120.1
C1 C6 H6 120.1
N1 C7 C8 105.50(14)
N1 C7 C17 125.62(14)
C8 C7 C17 128.78(14)
N3 C8 C7 121.12(15)
N3 C8 C9 132.44(14)
C7 C8 C9 106.44(13)
N2 C9 C8 110.24(14)
N2 C9 C16 119.67(15)
C8 C9 C16 130.08(14)
C11 C10 C15 117.30(14)
C11 C10 N4 123.58(14)
C15 C10 N4 118.56(15)
C12 C11 C10 120.64(15)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 120.83(17)
C11 C12 H12 119.6
C13 C12 H12 119.6
C14 C13 C12 119.82(16)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 118.85(16)
C13 C14 H14 120.6
C15 C14 H14 120.6
C14 C15 C10 122.54(16)
C14 C15 N5 117.41(14)
C10 C15 N5 120.04(14)
C9 C16 H16A 109.5
C9 C16 H16B 109.5
H16A C16 H16B 109.5
C9 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C7 C17 H17A 109.5
C7 C17 H17B 109.5
H17A C17 H17B 109.5
C7 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.7398(17)
O1 N5 1.2214(18)
O2 N5 1.2305(17)
N1 C7 1.355(2)
N1 N2 1.3889(18)
N1 C1 1.431(2)
N2 C9 1.329(2)
N3 N4 1.2761(18)
N3 C8 1.391(2)
N4 C10 1.430(2)
N5 C15 1.475(2)
C1 C2 1.387(2)
C1 C6 1.393(2)
C2 C3 1.384(2)
C2 H2 0.9500
C3 C4 1.394(2)
C3 H3 0.9500
C4 C5 1.384(2)
C5 C6 1.388(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.391(2)
C7 C17 1.490(2)
C8 C9 1.429(2)
C9 C16 1.498(2)
C10 C11 1.394(2)
C10 C15 1.395(2)
C11 C12 1.379(2)
C11 H11 0.9500
C12 C13 1.392(2)
C12 H12 0.9500
C13 C14 1.375(2)
C13 H13 0.9500
C14 C15 1.388(2)
C14 H14 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C17 H17A O1 5_666 0.98 2.52 3.478(2) 165
C12 H12 Cg3 8_655 0.93 2.87 3.689(2) 145
C17 H17C Cg1 8_655 0.96 2.93 3.838(2) 154
