#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226857.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_2226857
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Pek, Albert E.'
'Samshuddin, S.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 1-[3,5-Bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone
;
_journal_coeditor_code           FJ2320
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1950
_journal_page_last               o1951
_journal_paper_doi               10.1107/S1600536810025584
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 Cl2 N2 O'
_chemical_formula_moiety         'C17 H14 Cl2 N2 O'
_chemical_formula_sum            'C17 H14 Cl2 N2 O'
_chemical_formula_weight         333.20
_chemical_name_systematic
;
1-[3,5-Bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.412(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0716(9)
_cell_length_b                   13.160(2)
_cell_length_c                   19.782(3)
_cell_measurement_reflns_used    6706
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.84
_cell_measurement_theta_min      2.59
_cell_volume                     1563.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18906
_diffrn_reflns_theta_full        31.32
_diffrn_reflns_theta_max         31.32
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.417
_exptl_absorpt_correction_T_max  0.9174
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(APEX2; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.262
_refine_ls_goodness_of_fit_ref   1.442
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.442
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                4141
_reflns_number_total             4809
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2320.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226857
_cod_database_fobs_code          2226857
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_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.05600(5) 0.67498(2) 0.037299(16) 0.02593(9) Uani d . 1 . .
Cl Cl2 1.07200(6) 0.31318(3) 0.545917(17) 0.03442(10) Uani d . 1 . .
O O1 1.42292(14) 0.36398(8) 0.25597(5) 0.0284(2) Uani d . 1 . .
N N1 1.10312(16) 0.44665(8) 0.22241(5) 0.0223(2) Uani d . 1 . .
N N2 0.90756(16) 0.45866(8) 0.17716(5) 0.0215(2) Uani d . 1 . .
C C1 0.80954(19) 0.53952(9) 0.19412(6) 0.0198(2) Uani d . 1 . .
C C2 0.93583(19) 0.59546(9) 0.25404(6) 0.0227(2) Uani d . 1 . .
H H2A 0.8438 0.6066 0.2895 0.027 Uiso calc R 1 . .
H H2B 0.9900 0.6604 0.2401 0.027 Uiso calc R 1 . .
C C3 1.13032(19) 0.52236(9) 0.27851(6) 0.0205(2) Uani d . 1 . .
H H3 1.2730 0.5578 0.2802 0.025 Uiso calc R 1 . .
C C4 1.11491(18) 0.47227(8) 0.34639(6) 0.0185(2) Uani d . 1 . .
C C5 1.29877(19) 0.46775(9) 0.39706(6) 0.0204(2) Uani d . 1 . .
H H5 1.4322 0.4973 0.3895 0.024 Uiso calc R 1 . .
C C6 1.2861(2) 0.41974(9) 0.45879(6) 0.0226(2) Uani d . 1 . .
H H6 1.4100 0.4164 0.4924 0.027 Uiso calc R 1 . .
C C7 1.0866(2) 0.37695(9) 0.46945(6) 0.0227(2) Uani d . 1 . .
C C8 0.9003(2) 0.38125(9) 0.42023(6) 0.0239(2) Uani d . 1 . .
H H8 0.7665 0.3528 0.4285 0.029 Uiso calc R 1 . .
C C9 0.91492(19) 0.42834(9) 0.35855(6) 0.0218(2) Uani d . 1 . .
H H9 0.7908 0.4308 0.3249 0.026 Uiso calc R 1 . .
C C10 0.59722(19) 0.57204(8) 0.15606(6) 0.0189(2) Uani d . 1 . .
C C11 0.4946(2) 0.51628(9) 0.10008(6) 0.0230(2) Uani d . 1 . .
H H11 0.5614 0.4571 0.0874 0.028 Uiso calc R 1 . .
C C12 0.2948(2) 0.54783(9) 0.06325(6) 0.0236(2) Uani d . 1 . .
H H12 0.2282 0.5108 0.0257 0.028 Uiso calc R 1 . .
C C13 0.19554(19) 0.63577(9) 0.08334(6) 0.0200(2) Uani d . 1 . .
C C14 0.2917(2) 0.69243(9) 0.13857(6) 0.0214(2) Uani d . 1 . .
H H14 0.2227 0.7510 0.1515 0.026 Uiso calc R 1 . .
C C15 0.4939(2) 0.66028(9) 0.17462(6) 0.0214(2) Uani d . 1 . .
H H15 0.5610 0.6982 0.2116 0.026 Uiso calc R 1 . .
C C16 1.2506(2) 0.37105(9) 0.21546(6) 0.0233(2) Uani d . 1 . .
C C17 1.1866(2) 0.29880(10) 0.15692(6) 0.0307(3) Uani d . 1 . .
H H17A 1.3052 0.2512 0.1549 0.046 Uiso calc R 1 . .
H H17B 1.1597 0.3363 0.1149 0.046 Uiso calc R 1 . .
H H17C 1.0539 0.2628 0.1636 0.046 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 N1 N2 . . 122.18(10) ?
C16 N1 C3 . . 124.39(10) ?
N2 N1 C3 . . 113.42(9) ?
C1 N2 N1 . . 108.10(10) ?
N2 C1 C10 . . 121.01(11) ?
N2 C1 C2 . . 114.05(10) ?
C10 C1 C2 . . 124.93(10) ?
C1 C2 C3 . . 102.71(9) ?
C1 C2 H2A . . 111.2 ?
C3 C2 H2A . . 111.2 ?
C1 C2 H2B . . 111.2 ?
C3 C2 H2B . . 111.2 ?
H2A C2 H2B . . 109.1 ?
N1 C3 C4 . . 110.94(9) ?
N1 C3 C2 . . 100.81(9) ?
C4 C3 C2 . . 113.97(9) ?
N1 C3 H3 . . 110.3 ?
C4 C3 H3 . . 110.3 ?
C2 C3 H3 . . 110.3 ?
C5 C4 C9 . . 119.03(10) ?
C5 C4 C3 . . 120.83(10) ?
C9 C4 C3 . . 120.13(10) ?
C6 C5 C4 . . 120.86(11) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C7 C6 C5 . . 118.91(11) ?
C7 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C6 C7 C8 . . 121.49(11) ?
C6 C7 Cl2 . . 119.10(10) ?
C8 C7 Cl2 . . 119.39(9) ?
C7 C8 C9 . . 119.23(11) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
C8 C9 C4 . . 120.47(11) ?
C8 C9 H9 . . 119.8 ?
C4 C9 H9 . . 119.8 ?
C15 C10 C11 . . 118.71(11) ?
C15 C10 C1 . . 120.40(11) ?
C11 C10 C1 . . 120.88(10) ?
C12 C11 C10 . . 120.98(11) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C11 C12 C13 . . 118.86(11) ?
C11 C12 H12 . . 120.6 ?
C13 C12 H12 . . 120.6 ?
C14 C13 C12 . . 121.71(11) ?
C14 C13 Cl1 . . 119.46(9) ?
C12 C13 Cl1 . . 118.82(9) ?
C13 C14 C15 . . 118.71(11) ?
C13 C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C14 C15 C10 . . 121.01(11) ?
C14 C15 H15 . . 119.5 ?
C10 C15 H15 . . 119.5 ?
O1 C16 N1 . . 120.13(12) ?
O1 C16 C17 . . 123.72(11) ?
N1 C16 C17 . . 116.14(11) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C13 . 1.7382(12) ?
Cl2 C7 . 1.7435(12) ?
O1 C16 . 1.2249(15) ?
N1 C16 . 1.3588(15) ?
N1 N2 . 1.3875(14) ?
N1 C3 . 1.4826(15) ?
N2 C1 . 1.2875(14) ?
C1 C10 . 1.4587(16) ?
C1 C2 . 1.5063(16) ?
C2 C3 . 1.5449(16) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.5110(16) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.3881(16) ?
C4 C9 . 1.3972(16) ?
C5 C6 . 1.3871(16) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3795(17) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.3817(17) ?
C8 C9 . 1.3829(17) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C15 . 1.3946(16) ?
C10 C11 . 1.3968(16) ?
C11 C12 . 1.3842(17) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3895(16) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.3799(17) ?
C14 C15 . 1.3923(17) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.5049(18) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
C8 H8 Cl1 2_545 0.93 2.80 3.5996(13) 145
C9 H9 O1 1_455 0.93 2.59 3.4620(15) 156
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 N1 N2 C1 . . . . -176.08(10) ?
C3 N1 N2 C1 . . . . 5.01(13) ?
N1 N2 C1 C10 . . . . -179.54(10) ?
N1 N2 C1 C2 . . . . 1.70(13) ?
N2 C1 C2 C3 . . . . -7.14(13) ?
C10 C1 C2 C3 . . . . 174.16(10) ?
C16 N1 C3 C4 . . . . -66.76(14) ?
N2 N1 C3 C4 . . . . 112.11(10) ?
C16 N1 C3 C2 . . . . 172.18(11) ?
N2 N1 C3 C2 . . . . -8.95(12) ?
C1 C2 C3 N1 . . . . 8.80(11) ?
C1 C2 C3 C4 . . . . -110.09(11) ?
N1 C3 C4 C5 . . . . 113.38(12) ?
C2 C3 C4 C5 . . . . -133.67(11) ?
N1 C3 C4 C9 . . . . -65.65(13) ?
C2 C3 C4 C9 . . . . 47.30(15) ?
C9 C4 C5 C6 . . . . 0.53(17) ?
C3 C4 C5 C6 . . . . -178.51(11) ?
C4 C5 C6 C7 . . . . -0.50(17) ?
C5 C6 C7 C8 . . . . -0.21(18) ?
C5 C6 C7 Cl2 . . . . 178.08(9) ?
C6 C7 C8 C9 . . . . 0.87(18) ?
Cl2 C7 C8 C9 . . . . -177.42(9) ?
C7 C8 C9 C4 . . . . -0.83(18) ?
C5 C4 C9 C8 . . . . 0.14(17) ?
C3 C4 C9 C8 . . . . 179.19(11) ?
N2 C1 C10 C15 . . . . -179.43(11) ?
C2 C1 C10 C15 . . . . -0.81(17) ?
N2 C1 C10 C11 . . . . -0.06(17) ?
C2 C1 C10 C11 . . . . 178.56(11) ?
C15 C10 C11 C12 . . . . 0.38(18) ?
C1 C10 C11 C12 . . . . -179.00(11) ?
C10 C11 C12 C13 . . . . -0.77(18) ?
C11 C12 C13 C14 . . . . 0.43(18) ?
C11 C12 C13 Cl1 . . . . -179.69(9) ?
C12 C13 C14 C15 . . . . 0.28(18) ?
Cl1 C13 C14 C15 . . . . -179.60(9) ?
C13 C14 C15 C10 . . . . -0.67(18) ?
C11 C10 C15 C14 . . . . 0.35(17) ?
C1 C10 C15 C14 . . . . 179.73(11) ?
N2 N1 C16 O1 . . . . 178.94(10) ?
C3 N1 C16 O1 . . . . -2.28(18) ?
N2 N1 C16 C17 . . . . -1.78(16) ?
C3 N1 C16 C17 . . . . 177.00(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2236001
2 PubChem 1264654
