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#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102325.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_8102325
loop_
_publ_author_name
'Xiao-Yang Qiu'
'Xiu-Yun Ding'
'Mei-Rong Dong'
'Juan-Juan Liu'
_publ_section_title
;
 Crystal structure of
 4-1-(2-methoxynaphthalen-1-yl)-methylidene]amino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
 methanol solvate, C23H21N3O2 · CH3OH
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              407
_journal_volume                  223
_journal_year                    2008
_chemical_formula_sum            'C24 H25 N3 O3'
_chemical_formula_weight         403.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 93.394(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.958(5)
_cell_length_b                   8.185(4)
_cell_length_c                   24.354(11)
_cell_measurement_reflns_used    1762
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      2.4
_cell_volume                     2180.5(18)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 [9]'
_computing_structure_solution    'SHELXS-97 [8]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8832
_diffrn_reflns_theta_full        23.07
_diffrn_reflns_theta_max         23.07
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0425
_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)+(0.0537P)²+0.3096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2073
_reflns_number_total             3022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2359.cff
_cod_data_source_block           qiu
_cod_original_cell_volume        2180.3(17)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8102325
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36129(14) 0.4821(2) 0.17912(6) 0.0757(5) Uani 1 1 d . . .
O2 O 0.32372(15) 0.1489(2) 0.05281(6) 0.0779(5) Uani 1 1 d . . .
O3 O 0.1262(2) 0.2891(5) 0.09952(12) 0.1576(11) Uani 1 1 d . . .
H3 H 0.1891 0.2520 0.0877 0.236 Uiso 1 1 calc R . .
N1 N 0.57812(16) 0.3214(2) 0.07515(7) 0.0623(5) Uani 1 1 d . . .
N2 N 0.3821(2) 0.1585(2) -0.03689(7) 0.0715(6) Uani 1 1 d . . .
N3 N 0.4799(2) 0.2277(2) -0.06337(8) 0.0738(6) Uani 1 1 d . . .
C1 C 0.56388(18) 0.4037(2) 0.17037(8) 0.0514(5) Uani 1 1 d . . .
C2 C 0.4787(2) 0.4805(2) 0.20131(9) 0.0572(6) Uani 1 1 d . . .
C3 C 0.5127(2) 0.5581(3) 0.25129(10) 0.0702(7) Uani 1 1 d . . .
H3A H 0.4540 0.6098 0.2712 0.084 Uiso 1 1 calc R . .
C4 C 0.6308(2) 0.5573(3) 0.27037(10) 0.0731(7) Uani 1 1 d . . .
H4 H 0.6528 0.6116 0.3030 0.088 Uiso 1 1 calc R . .
C5 C 0.7214(2) 0.4767(3) 0.24234(9) 0.0647(6) Uani 1 1 d . . .
C6 C 0.8440(3) 0.4677(4) 0.26384(11) 0.0866(8) Uani 1 1 d . . .
H6 H 0.8667 0.5227 0.2963 0.104 Uiso 1 1 calc R . .
C7 C 0.9289(2) 0.3810(4) 0.23833(13) 0.0962(9) Uani 1 1 d . . .
H7 H 1.0088 0.3761 0.2533 0.115 Uiso 1 1 calc R . .
C8 C 0.8967(2) 0.2989(4) 0.18957(12) 0.0916(9) Uani 1 1 d . . .
H8 H 0.9552 0.2375 0.1726 0.110 Uiso 1 1 calc R . .
C9 C 0.7799(2) 0.3073(3) 0.16622(10) 0.0713(7) Uani 1 1 d . . .
H9 H 0.7607 0.2534 0.1332 0.086 Uiso 1 1 calc R . .
C10 C 0.68806(19) 0.3967(2) 0.19162(9) 0.0567(6) Uani 1 1 d . . .
C11 C 0.2640(2) 0.5185(4) 0.21282(12) 0.0994(9) Uani 1 1 d . . .
H11A H 0.2725 0.4548 0.2459 0.149 Uiso 1 1 calc R . .
H11B H 0.1876 0.4928 0.1934 0.149 Uiso 1 1 calc R . .
H11C H 0.2659 0.6326 0.2220 0.149 Uiso 1 1 calc R . .
C12 C 0.51727(19) 0.3334(2) 0.11797(8) 0.0560(5) Uani 1 1 d . . .
H12 H 0.4373 0.2946 0.1158 0.067 Uiso 1 1 calc R . .
C13 C 0.5183(2) 0.2618(3) 0.02681(9) 0.0592(6) Uani 1 1 d . . .
C14 C 0.4011(2) 0.1864(3) 0.01951(9) 0.0635(6) Uani 1 1 d . . .
C15 C 0.5635(2) 0.2784(3) -0.02396(9) 0.0669(6) Uani 1 1 d . . .
C16 C 0.6845(2) 0.3416(4) -0.03807(11) 0.0933(8) Uani 1 1 d . . .
H16A H 0.7336 0.2530 -0.0502 0.140 Uiso 1 1 calc R . .
H16B H 0.7245 0.3916 -0.0062 0.140 Uiso 1 1 calc R . .
H16C H 0.6738 0.4211 -0.0669 0.140 Uiso 1 1 calc R . .
C17 C 0.5082(3) 0.1556(3) -0.11643(9) 0.0970(9) Uani 1 1 d . . .
H17A H 0.5632 0.2260 -0.1345 0.146 Uiso 1 1 calc R . .
H17B H 0.4341 0.1429 -0.1391 0.146 Uiso 1 1 calc R . .
H17C H 0.5458 0.0507 -0.1103 0.146 Uiso 1 1 calc R . .
C18 C 0.2630(3) 0.1599(3) -0.06393(9) 0.0726(7) Uani 1 1 d . . .
C19 C 0.1817(3) 0.0389(3) -0.05266(12) 0.1008(10) Uani 1 1 d . . .
H19 H 0.2060 -0.0467 -0.0294 0.121 Uiso 1 1 calc R . .
C20 C 0.0640(3) 0.0443(4) -0.07588(14) 0.1175(11) Uani 1 1 d . . .
H20 H 0.0080 -0.0361 -0.0676 0.141 Uiso 1 1 calc R . .
C21 C 0.0295(3) 0.1689(5) -0.11140(13) 0.1136(11) Uani 1 1 d . . .
H21 H -0.0496 0.1722 -0.1275 0.136 Uiso 1 1 calc R . .
C22 C 0.1106(3) 0.2859(4) -0.12277(13) 0.1131(11) Uani 1 1 d . . .
H22 H 0.0872 0.3689 -0.1473 0.136 Uiso 1 1 calc R . .
C23 C 0.2271(3) 0.2848(3) -0.09882(11) 0.0936(8) Uani 1 1 d . . .
H23 H 0.2815 0.3682 -0.1062 0.112 Uiso 1 1 calc R . .
C24 C 0.0582(4) 0.3677(5) 0.0570(2) 0.1634(17) Uani 1 1 d . . .
H24A H -0.0274 0.3561 0.0625 0.245 Uiso 1 1 calc R . .
H24B H 0.0761 0.3194 0.0224 0.245 Uiso 1 1 calc R . .
H24C H 0.0793 0.4815 0.0568 0.245 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C11 119.80(18) . . ?
C24 O3 H3 109.5 . . ?
C12 N1 C13 118.22(19) . . ?
C14 N2 N3 108.18(19) . . ?
C14 N2 C18 122.2(2) . . ?
N3 N2 C18 119.19(18) . . ?
C15 N3 N2 107.56(18) . . ?
C15 N3 C17 125.3(2) . . ?
N2 N3 C17 116.6(2) . . ?
C2 C1 C10 118.64(19) . . ?
C2 C1 C12 116.18(19) . . ?
C10 C1 C12 125.18(19) . . ?
O1 C2 C1 116.00(19) . . ?
O1 C2 C3 122.3(2) . . ?
C1 C2 C3 121.7(2) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 121.8(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 C10 119.0(2) . . ?
C6 C5 C10 119.1(2) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 117.6(2) . . ?
C9 C10 C1 123.3(2) . . ?
C5 C10 C1 119.0(2) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C1 124.8(2) . . ?
N1 C12 H12 117.6 . . ?
C1 C12 H12 117.6 . . ?
C15 C13 N1 123.3(2) . . ?
C15 C13 C14 107.6(2) . . ?
N1 C13 C14 129.0(2) . . ?
O2 C14 N2 122.1(2) . . ?
O2 C14 C13 131.9(2) . . ?
N2 C14 C13 106.0(2) . . ?
N3 C15 C13 110.2(2) . . ?
N3 C15 C16 121.3(2) . . ?
C13 C15 C16 128.4(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.8(3) . . ?
C19 C18 N2 119.3(2) . . ?
C23 C18 N2 120.8(2) . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 119.5(3) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.366(2) . ?
O1 C11 1.415(3) . ?
O2 C14 1.246(2) . ?
O3 C24 1.396(5) . ?
O3 H3 0.8200 . ?
N1 C12 1.274(2) . ?
N1 C13 1.401(3) . ?
N2 C14 1.396(3) . ?
N2 N3 1.403(3) . ?
N2 C18 1.427(3) . ?
N3 C15 1.352(3) . ?
N3 C17 1.470(3) . ?
C1 C2 1.385(3) . ?
C1 C10 1.428(3) . ?
C1 C12 1.464(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.350(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.402(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(3) . ?
C5 C10 1.427(3) . ?
C6 C7 1.350(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.416(3) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 C15 1.366(3) . ?
C13 C14 1.426(3) . ?
C15 C16 1.483(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.370(3) . ?
C18 C23 1.372(3) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.347(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.94 2.754(3) 172.4 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653947
