#------------------------------------------------------------------------------
#$Date: 2021-01-30 08:28:00 +0200 (Sat, 30 Jan 2021) $
#$Revision: 261326 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560235.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_1560235
loop_
_publ_author_name
'Yoo, Miri'
'Koh, Dongsoo'
_publ_section_title
;
 1-[5-(3,5-Dimethoxyphenyl)-3-(2-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone
;
_journal_coeditor_code           HB4374
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x210096
_journal_paper_doi               10.1107/S2414314621000961
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C20 H22 N2 O4'
_chemical_formula_moiety         'C20 H22 N2 O4'
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.39
_chemical_name_systematic
1-[5-(3,5-Dimethoxyphenyl)-3-(2-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                113.0348(10)
_cell_angle_beta                 91.4395(12)
_cell_angle_gamma                107.4022(11)
_cell_formula_units_Z            2
_cell_length_a                   8.7181(2)
_cell_length_b                   10.7230(3)
_cell_length_c                   11.2096(3)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.27
_cell_volume                     908.09(4)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39068
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         2.191
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       Block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.3528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                3338
_reflns_number_total             4541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4374sup1.cif
_cod_data_source_block           I
_cod_database_code               1560235
_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.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.33313(18) 0.31123(16) 0.49923(14) 0.0328(3) Uani d 1 . .
C C2 0.28231(17) 0.40413(15) 0.46044(13) 0.0290(3) Uani d 1 . .
C C3 0.20042(19) 0.48741(17) 0.54478(14) 0.0349(3) Uani d 1 . .
H H3 0.1650 0.5503 0.5209 0.042 Uiso calc 1 . .
C C4 0.1704(2) 0.47940(19) 0.66259(16) 0.0423(4) Uani d 1 . .
H H4 0.1143 0.5357 0.7174 0.051 Uiso calc 1 . .
C C5 0.2233(2) 0.38832(19) 0.69949(16) 0.0439(4) Uani d 1 . .
H H5 0.2041 0.3837 0.7800 0.053 Uiso calc 1 . .
C C6 0.3037(2) 0.30458(18) 0.61869(15) 0.0391(4) Uani d 1 . .
H H6 0.3390 0.2426 0.6441 0.047 Uiso calc 1 . .
O O1 0.41126(15) 0.23045(13) 0.41477(11) 0.0445(3) Uani d 1 . .
C C7 0.4509(3) 0.1255(2) 0.4431(2) 0.0658(6) Uani d 1 . .
H H7A 0.5253 0.1720 0.5256 0.099 Uiso calc 1 . .
H H7B 0.5023 0.0745 0.3733 0.099 Uiso calc 1 . .
H H7C 0.3525 0.0580 0.4498 0.099 Uiso calc 1 . .
C C8 0.30805(17) 0.41521(15) 0.33494(13) 0.0274(3) Uani d 1 . .
C C9 0.38469(18) 0.32990(16) 0.22753(13) 0.0304(3) Uani d 1 . .
H H9A 0.3314 0.2262 0.1994 0.037 Uiso calc 1 . .
H H9B 0.5013 0.3553 0.2562 0.037 Uiso calc 1 . .
C C10 0.35565(17) 0.37553(15) 0.11689(13) 0.0285(3) Uani d 1 . .
H H10 0.4592 0.4092 0.0863 0.034 Uiso calc 1 . .
N N1 0.29693(15) 0.49645(12) 0.18619(11) 0.0297(3) Uani d 1 . .
N N2 0.26272(15) 0.50766(13) 0.31007(11) 0.0298(3) Uani d 1 . .
C C11 0.22958(17) 0.25555(14) 0.00294(13) 0.0277(3) Uani d 1 . .
C C12 0.27974(18) 0.17696(15) -0.10909(14) 0.0304(3) Uani d 1 . .
H H12 0.3907 0.2019 -0.1172 0.036 Uiso calc 1 . .
C C13 0.16453(19) 0.06023(16) -0.21028(14) 0.0339(3) Uani d 1 . .
C C14 0.00146(19) 0.02227(16) -0.20007(15) 0.0358(3) Uani d 1 . .
H H14 -0.0754 -0.0568 -0.2686 0.043 Uiso calc 1 . .
C C15 -0.04762(18) 0.10307(15) -0.08643(15) 0.0325(3) Uani d 1 . .
C C16 0.06497(18) 0.21904(15) 0.01496(14) 0.0312(3) Uani d 1 . .
H H16 0.0309 0.2729 0.0914 0.037 Uiso calc 1 . .
O O2 0.22721(16) -0.01188(13) -0.31699(11) 0.0514(3) Uani d 1 . .
C C17 0.1152(3) -0.1365(3) -0.4194(2) 0.0962(10) Uani d 1 . .
H H17A 0.0575 -0.2030 -0.3836 0.144 Uiso calc 1 . .
H H17B 0.1739 -0.1825 -0.4857 0.144 Uiso calc 1 . .
H H17C 0.0378 -0.1091 -0.4586 0.144 Uiso calc 1 . .
O O3 -0.21162(13) 0.05856(12) -0.08562(12) 0.0446(3) Uani d 1 . .
C C18 -0.2693(2) 0.1386(2) 0.0275(2) 0.0499(4) Uani d 1 . .
H H18A -0.2214 0.1346 0.1043 0.075 Uiso calc 1 . .
H H18B -0.3870 0.0978 0.0156 0.075 Uiso calc 1 . .
H H18C -0.2387 0.2380 0.0394 0.075 Uiso calc 1 . .
C C19 0.26834(19) 0.58262(16) 0.13306(14) 0.0332(3) Uani d 1 . .
O O4 0.29910(15) 0.56660(13) 0.02318(11) 0.0439(3) Uani d 1 . .
C C20 0.1993(3) 0.6953(2) 0.21300(18) 0.0534(5) Uani d 1 . .
H H20A 0.2756 0.7898 0.2308 0.080 Uiso calc 1 . .
H H20B 0.1805 0.6879 0.2953 0.080 Uiso calc 1 . .
H H20C 0.0971 0.6813 0.1647 0.080 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'
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
O1 C1 C6 . . 123.01(14) ?
O1 C1 C2 . . 116.47(13) ?
C6 C1 C2 . . 120.52(14) ?
C3 C2 C1 . . 117.68(13) ?
C3 C2 C8 . . 119.07(13) ?
C1 C2 C8 . . 123.24(13) ?
C4 C3 C2 . . 121.49(15) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 119.82(15) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C6 C5 C4 . . 120.19(14) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 120.29(15) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
C1 O1 C7 . . 118.67(14) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C2 . . 118.77(12) ?
N2 C8 C9 . . 113.69(12) ?
C2 C8 C9 . . 127.53(12) ?
C8 C9 C10 . . 102.65(11) ?
C8 C9 H9A . . 111.2 ?
C10 C9 H9A . . 111.2 ?
C8 C9 H9B . . 111.2 ?
C10 C9 H9B . . 111.2 ?
H9A C9 H9B . . 109.2 ?
N1 C10 C11 . . 111.67(12) ?
N1 C10 C9 . . 101.24(10) ?
C11 C10 C9 . . 112.00(11) ?
N1 C10 H10 . . 110.5 ?
C11 C10 H10 . . 110.5 ?
C9 C10 H10 . . 110.5 ?
C19 N1 N2 . . 122.73(12) ?
C19 N1 C10 . . 124.12(11) ?
N2 N1 C10 . . 113.02(11) ?
C8 N2 N1 . . 108.20(11) ?
C12 C11 C16 . . 120.38(13) ?
C12 C11 C10 . . 119.43(12) ?
C16 C11 C10 . . 120.06(12) ?
C11 C12 C13 . . 119.39(14) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
O2 C13 C14 . . 124.09(14) ?
O2 C13 C12 . . 114.83(14) ?
C14 C13 C12 . . 121.07(14) ?
C13 C14 C15 . . 118.92(14) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
O3 C15 C16 . . 124.38(14) ?
O3 C15 C14 . . 114.83(13) ?
C16 C15 C14 . . 120.79(14) ?
C15 C16 C11 . . 119.44(13) ?
C15 C16 H16 . . 120.3 ?
C11 C16 H16 . . 120.3 ?
C13 O2 C17 . . 116.73(15) ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 O3 C18 . . 117.33(13) ?
O3 C18 H18A . . 109.5 ?
O3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O4 C19 N1 . . 119.79(14) ?
O4 C19 C20 . . 122.44(14) ?
N1 C19 C20 . . 117.77(13) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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
C1 O1 . 1.3617(18) ?
C1 C6 . 1.395(2) ?
C1 C2 . 1.404(2) ?
C2 C3 . 1.398(2) ?
C2 C8 . 1.4746(19) ?
C3 C4 . 1.383(2) ?
C3 H3 . 0.9400 ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.9400 ?
C5 C6 . 1.375(2) ?
C5 H5 . 0.9400 ?
C6 H6 . 0.9400 ?
O1 C7 . 1.412(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C7 H7C . 0.9700 ?
C8 N2 . 1.2891(18) ?
C8 C9 . 1.5090(19) ?
C9 C10 . 1.5411(19) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C10 N1 . 1.4749(17) ?
C10 C11 . 1.5141(19) ?
C10 H10 . 0.9900 ?
N1 C19 . 1.3534(19) ?
N1 N2 . 1.3940(15) ?
C11 C12 . 1.3778(19) ?
C11 C16 . 1.395(2) ?
C12 C13 . 1.394(2) ?
C12 H12 . 0.9400 ?
C13 O2 . 1.3744(18) ?
C13 C14 . 1.378(2) ?
C14 C15 . 1.394(2) ?
C14 H14 . 0.9400 ?
C15 O3 . 1.3668(18) ?
C15 C16 . 1.382(2) ?
C16 H16 . 0.9400 ?
O2 C17 . 1.421(2) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 H17C . 0.9700 ?
O3 C18 . 1.427(2) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C18 H18C . 0.9700 ?
C19 O4 . 1.2236(17) ?
C19 C20 . 1.497(2) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C20 H20C . 0.9700 ?
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
C10 H10 O4 2_665 0.99 2.46 3.4340(18) 167
C5 H5 O4 1_556 0.94 2.59 3.309(2) 134
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
O1 C1 C2 C3 . . . . 179.43(13) ?
C6 C1 C2 C3 . . . . -0.7(2) ?
O1 C1 C2 C8 . . . . 0.8(2) ?
C6 C1 C2 C8 . . . . -179.33(14) ?
C1 C2 C3 C4 . . . . 0.2(2) ?
C8 C2 C3 C4 . . . . 178.85(14) ?
C2 C3 C4 C5 . . . . 0.6(2) ?
C3 C4 C5 C6 . . . . -0.8(3) ?
C4 C5 C6 C1 . . . . 0.3(3) ?
O1 C1 C6 C5 . . . . -179.62(15) ?
C2 C1 C6 C5 . . . . 0.5(2) ?
C6 C1 O1 C7 . . . . 6.1(2) ?
C2 C1 O1 C7 . . . . -174.01(16) ?
C3 C2 C8 N2 . . . . 4.0(2) ?
C1 C2 C8 N2 . . . . -177.35(14) ?
C3 C2 C8 C9 . . . . -176.46(14) ?
C1 C2 C8 C9 . . . . 2.2(2) ?
N2 C8 C9 C10 . . . . -7.73(16) ?
C2 C8 C9 C10 . . . . 172.73(13) ?
C8 C9 C10 N1 . . . . 10.06(13) ?
C8 C9 C10 C11 . . . . -109.04(12) ?
C11 C10 N1 C19 . . . . -67.02(17) ?
C9 C10 N1 C19 . . . . 173.65(13) ?
C11 C10 N1 N2 . . . . 108.85(13) ?
C9 C10 N1 N2 . . . . -10.49(15) ?
C2 C8 N2 N1 . . . . -179.04(12) ?
C9 C8 N2 N1 . . . . 1.37(16) ?
C19 N1 N2 C8 . . . . -177.84(13) ?
C10 N1 N2 C8 . . . . 6.23(16) ?
N1 C10 C11 C12 . . . . 145.36(13) ?
C9 C10 C11 C12 . . . . -101.88(15) ?
N1 C10 C11 C16 . . . . -38.83(17) ?
C9 C10 C11 C16 . . . . 73.92(16) ?
C16 C11 C12 C13 . . . . -0.2(2) ?
C10 C11 C12 C13 . . . . 175.58(13) ?
C11 C12 C13 O2 . . . . -179.32(13) ?
C11 C12 C13 C14 . . . . 0.0(2) ?
O2 C13 C14 C15 . . . . 179.53(14) ?
C12 C13 C14 C15 . . . . 0.2(2) ?
C13 C14 C15 O3 . . . . 179.30(13) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
O3 C15 C16 C11 . . . . -179.44(13) ?
C14 C15 C16 C11 . . . . 0.1(2) ?
C12 C11 C16 C15 . . . . 0.1(2) ?
C10 C11 C16 C15 . . . . -175.64(13) ?
C14 C13 O2 C17 . . . . -2.7(3) ?
C12 C13 O2 C17 . . . . 176.6(2) ?
C16 C15 O3 C18 . . . . 0.5(2) ?
C14 C15 O3 C18 . . . . -179.07(14) ?
N2 N1 C19 O4 . . . . -179.14(14) ?
C10 N1 C19 O4 . . . . -3.7(2) ?
N2 N1 C19 C20 . . . . 0.9(2) ?
C10 N1 C19 C20 . . . . 176.37(15) ?

_cod_database_fobs_code 1560235
