#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233129.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_2233129
loop_
_publ_author_name
'Yang, Xiao-Li'
_publ_section_title
;
 Ethyl 2-{[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate
;
_journal_coeditor_code           EZ2274
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o123
_journal_paper_doi               10.1107/S1600536811052937
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H17 Cl N2 O3'
_chemical_formula_moiety         'C19 H17 Cl N2 O3'
_chemical_formula_sum            'C19 H17 Cl N2 O3'
_chemical_formula_weight         356.80
_chemical_melting_point          369
_chemical_name_systematic
;
Ethyl 2-{[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6158(11)
_cell_length_b                   15.9119(16)
_cell_length_c                   19.302(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     3567.6(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0923
_diffrn_reflns_av_sigmaI/netI    0.1023
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6360
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0551
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1787
_reflns_number_total             3244
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ez2274.cif
_cod_data_source_block           I
_cod_database_code               2233129
_cod_database_fobs_code          2233129
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'
'-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_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_symmetry_multiplicity
Cl Cl 0.35737(6) 0.17569(5) 0.39581(4) 0.0686(3) Uani d . 1 1
O O1 0.00916(16) 0.53604(11) 0.21036(10) 0.0628(6) Uani d . 1 1
N N1 -0.10819(17) 0.42944(13) 0.25540(13) 0.0491(6) Uani d . 1 1
C C1 0.0080(2) 0.28411(17) 0.43656(13) 0.0535(8) Uani d . 1 1
H H1B -0.0653 0.3054 0.4447 0.064 Uiso calc R 1 1
N N2 -0.08809(16) 0.36663(13) 0.30241(11) 0.0453(6) Uani d . 1 1
O O2 -0.18554(18) 0.49472(12) 0.07176(11) 0.0641(6) Uani d . 1 1
C C2 0.0559(2) 0.22869(18) 0.48294(14) 0.0575(8) Uani d . 1 1
H H2A 0.0148 0.2126 0.5221 0.069 Uiso calc R 1 1
C C3 0.1657(2) 0.19648(16) 0.47169(14) 0.0516(8) Uani d . 1 1
H H3A 0.1989 0.1599 0.5035 0.062 Uiso calc R 1 1
O O3 -0.0121(2) 0.43762(13) 0.09175(12) 0.0896(8) Uani d . 1 1
C C4 0.2242(2) 0.21959(16) 0.41286(14) 0.0450(7) Uani d . 1 1
C C5 0.1774(2) 0.27566(16) 0.36660(13) 0.0421(7) Uani d . 1 1
H H5A 0.2190 0.2917 0.3276 0.050 Uiso calc R 1 1
C C6 0.0677(2) 0.30848(16) 0.37803(13) 0.0417(7) Uani d . 1 1
C C7 0.0204(2) 0.36878(17) 0.32760(13) 0.0423(6) Uani d . 1 1
C C8 0.0733(2) 0.43603(16) 0.29721(14) 0.0506(7) Uani d . 1 1
H H8A 0.1480 0.4552 0.3045 0.061 Uiso calc R 1 1
C C9 -0.0090(2) 0.46931(16) 0.25317(15) 0.0485(7) Uani d . 1 1
C C10 -0.1769(2) 0.30433(16) 0.31081(14) 0.0417(7) Uani d . 1 1
C C11 -0.2865(2) 0.32957(17) 0.32679(13) 0.0478(7) Uani d . 1 1
H H11A -0.3019 0.3860 0.3351 0.057 Uiso calc R 1 1
C C12 -0.3740(2) 0.27127(18) 0.33060(15) 0.0530(8) Uani d . 1 1
H H12A -0.4489 0.2883 0.3400 0.064 Uiso calc R 1 1
C C13 -0.3490(2) 0.18712(18) 0.32025(15) 0.0571(8) Uani d . 1 1
H H13A -0.4074 0.1473 0.3235 0.068 Uiso calc R 1 1
C C14 -0.2385(2) 0.16216(18) 0.30514(15) 0.0590(8) Uani d . 1 1
H H14A -0.2223 0.1055 0.2987 0.071 Uiso calc R 1 1
C C15 -0.1520(2) 0.22070(16) 0.29954(14) 0.0492(7) Uani d . 1 1
H H15A -0.0775 0.2041 0.2883 0.059 Uiso calc R 1 1
C C16 -0.0794(2) 0.55185(16) 0.16175(16) 0.0583(8) Uani d . 1 1
H H16A -0.0667 0.6065 0.1408 0.070 Uiso calc R 1 1
H H16B -0.1526 0.5538 0.1859 0.070 Uiso calc R 1 1
C C17 -0.0859(3) 0.48651(18) 0.10533(17) 0.0572(8) Uani d . 1 1
C C18 -0.2018(3) 0.4426(2) 0.01132(19) 0.0866(11) Uani d . 1 1
H H18A -0.2028 0.3837 0.0243 0.104 Uiso calc R 1 1
H H18B -0.1396 0.4514 -0.0215 0.104 Uiso calc R 1 1
C C19 -0.3146(4) 0.4671(3) -0.0204(2) 0.1339(17) Uani d . 1 1
H H19A -0.3283 0.4337 -0.0609 0.201 Uiso calc R 1 1
H H19B -0.3124 0.5255 -0.0330 0.201 Uiso calc R 1 1
H H19C -0.3753 0.4580 0.0125 0.201 Uiso calc R 1 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'
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 0.0060 '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
C9 O1 C16 115.3(2)
C9 N1 N2 103.0(2)
C2 C1 C6 120.6(3)
C2 C1 H1B 119.7
C6 C1 H1B 119.7
C7 N2 N1 112.3(2)
C7 N2 C10 130.2(2)
N1 N2 C10 117.04(19)
C17 O2 C18 116.7(3)
C1 C2 C3 120.4(3)
C1 C2 H2A 119.8
C3 C2 H2A 119.8
C4 C3 C2 118.9(3)
C4 C3 H3A 120.5
C2 C3 H3A 120.5
C3 C4 C5 121.0(2)
C3 C4 Cl 119.5(2)
C5 C4 Cl 119.5(2)
C4 C5 C6 120.1(2)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
C1 C6 C5 118.9(2)
C1 C6 C7 122.4(2)
C5 C6 C7 118.7(2)
N2 C7 C8 106.6(2)
N2 C7 C6 124.7(2)
C8 C7 C6 128.7(2)
C7 C8 C9 104.6(2)
C7 C8 H8A 127.7
C9 C8 H8A 127.7
N1 C9 O1 122.1(2)
N1 C9 C8 113.6(2)
O1 C9 C8 124.3(2)
C11 C10 C15 120.9(2)
C11 C10 N2 119.3(2)
C15 C10 N2 119.7(2)
C10 C11 C12 120.0(3)
C10 C11 H11A 120.0
C12 C11 H11A 120.0
C11 C12 C13 119.3(3)
C11 C12 H12A 120.3
C13 C12 H12A 120.3
C14 C13 C12 120.3(3)
C14 C13 H13A 119.8
C12 C13 H13A 119.8
C15 C14 C13 120.2(3)
C15 C14 H14A 119.9
C13 C14 H14A 119.9
C14 C15 C10 119.2(2)
C14 C15 H15A 120.4
C10 C15 H15A 120.4
O1 C16 C17 113.1(2)
O1 C16 H16A 109.0
C17 C16 H16A 109.0
O1 C16 H16B 109.0
C17 C16 H16B 109.0
H16A C16 H16B 107.8
O3 C17 O2 125.8(3)
O3 C17 C16 125.1(3)
O2 C17 C16 109.1(3)
O2 C18 C19 107.1(3)
O2 C18 H18A 110.3
C19 C18 H18A 110.3
O2 C18 H18B 110.3
C19 C18 H18B 110.3
H18A C18 H18B 108.5
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C4 1.729(3)
O1 C9 1.362(3)
O1 C16 1.415(3)
N1 C9 1.316(3)
N1 N2 1.370(3)
C1 C2 1.374(3)
C1 C6 1.381(3)
C1 H1B 0.9300
N2 C7 1.351(3)
N2 C10 1.440(3)
O2 C17 1.333(3)
O2 C18 1.444(3)
C2 C3 1.391(4)
C2 H2A 0.9300
C3 C4 1.373(3)
C3 H3A 0.9300
O3 C17 1.188(3)
C4 C5 1.374(3)
C5 C6 1.394(3)
C5 H5A 0.9300
C6 C7 1.473(3)
C7 C8 1.367(3)
C8 C9 1.385(3)
C8 H8A 0.9300
C10 C11 1.370(3)
C10 C15 1.379(3)
C11 C12 1.378(3)
C11 H11A 0.9300
C12 C13 1.384(4)
C12 H12A 0.9300
C13 C14 1.375(3)
C13 H13A 0.9300
C14 C15 1.375(3)
C14 H14A 0.9300
C15 H15A 0.9300
C16 C17 1.508(4)
C16 H16A 0.9700
C16 H16B 0.9700
C18 C19 1.498(4)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
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
C9 N1 N2 C7 -0.1(3)
C9 N1 N2 C10 -172.7(2)
C6 C1 C2 C3 0.2(4)
C1 C2 C3 C4 -1.3(4)
C2 C3 C4 C5 2.0(4)
C2 C3 C4 Cl -176.5(2)
C3 C4 C5 C6 -1.6(4)
Cl C4 C5 C6 176.93(19)
C2 C1 C6 C5 0.2(4)
C2 C1 C6 C7 -179.0(2)
C4 C5 C6 C1 0.4(4)
C4 C5 C6 C7 179.7(2)
N1 N2 C7 C8 1.0(3)
C10 N2 C7 C8 172.4(2)
N1 N2 C7 C6 -178.9(2)
C10 N2 C7 C6 -7.6(4)
C1 C6 C7 N2 -45.5(4)
C5 C6 C7 N2 135.3(3)
C1 C6 C7 C8 134.5(3)
C5 C6 C7 C8 -44.7(4)
N2 C7 C8 C9 -1.5(3)
C6 C7 C8 C9 178.5(2)
N2 N1 C9 O1 178.1(2)
N2 N1 C9 C8 -0.9(3)
C16 O1 C9 N1 -8.7(4)
C16 O1 C9 C8 170.3(3)
C7 C8 C9 N1 1.6(3)
C7 C8 C9 O1 -177.5(2)
C7 N2 C10 C11 134.0(3)
N1 N2 C10 C11 -55.0(3)
C7 N2 C10 C15 -49.0(4)
N1 N2 C10 C15 122.0(3)
C15 C10 C11 C12 -1.1(4)
N2 C10 C11 C12 175.8(2)
C10 C11 C12 C13 2.0(4)
C11 C12 C13 C14 -1.1(5)
C12 C13 C14 C15 -0.6(5)
C13 C14 C15 C10 1.4(4)
C11 C10 C15 C14 -0.6(5)
N2 C10 C15 C14 -177.5(2)
C9 O1 C16 C17 -70.7(3)
C18 O2 C17 O3 -3.6(4)
C18 O2 C17 C16 174.0(2)
O1 C16 C17 O3 -16.5(4)
O1 C16 C17 O2 165.9(2)
C17 O2 C18 C19 -175.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657313
