#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224582.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_2224582
loop_
_publ_author_name
'Zhang, Li-Ping'
'Yang, Ming'
'Fang, Yun'
_publ_section_title
;
 (Z)-3-(4-Methoxyanilino)-1-phenylbut-2-en-1-one
;
_journal_coeditor_code           CI2973
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o7
_journal_paper_doi               10.1107/S1600536809051186
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H17 N O2'
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.32
_chemical_name_systematic
;
(Z)-3-(4-Methoxyanilino)-1-phenylbut-2-en-1-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.954(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.435(2)
_cell_length_b                   7.287(3)
_cell_length_c                   30.919(12)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.64
_cell_volume                     1444.4(9)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7729
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.166
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0459
_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)+(0.0645P)²+0.2627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                1900
_reflns_number_total             2931
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2973.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1444.5(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224582
_cod_database_fobs_code          2224582
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
O O1 0.0332(2) 0.1669(2) 0.45901(4) 0.0621(4) Uani d . 1 . .
O O2 -0.17087(19) 0.1729(2) 0.20705(4) 0.0552(4) Uani d . 1 . .
N N1 0.0723(2) 0.1693(2) 0.27987(4) 0.0417(4) Uani d . 1 . .
H H1 -0.0489 0.1722 0.2658 0.050 Uiso calc R 1 . .
C C1 0.0705(2) 0.1739(2) 0.32573(5) 0.0364(4) Uani d . 1 . .
C C2 -0.0759(3) 0.2824(3) 0.34338(5) 0.0412(4) Uani d . 1 . .
H H2 -0.1639 0.3558 0.3253 0.049 Uiso calc R 1 . .
C C3 -0.0940(3) 0.2835(3) 0.38775(5) 0.0445(5) Uani d . 1 . .
H H3 -0.1947 0.3560 0.3992 0.053 Uiso calc R 1 . .
C C4 0.0378(3) 0.1768(2) 0.41473(5) 0.0423(4) Uani d . 1 . .
C C5 0.1869(3) 0.0706(3) 0.39734(6) 0.0515(5) Uani d . 1 . .
H H5 0.2780 0.0005 0.4156 0.062 Uiso calc R 1 . .
C C6 0.2022(3) 0.0673(3) 0.35319(6) 0.0480(5) Uani d . 1 . .
H H6 0.3015 -0.0069 0.3418 0.058 Uiso calc R 1 . .
C C7 -0.1412(4) 0.2438(4) 0.47712(6) 0.0798(8) Uani d . 1 . .
H H7A -0.1385 0.3749 0.4740 0.120 Uiso calc R 1 . .
H H7B -0.1366 0.2126 0.5074 0.120 Uiso calc R 1 . .
H H7C -0.2670 0.1963 0.4623 0.120 Uiso calc R 1 . .
C C8 0.4516(3) 0.1682(3) 0.27522(6) 0.0504(5) Uani d . 1 . .
H H8A 0.4579 0.2429 0.3009 0.076 Uiso calc R 1 . .
H H8B 0.5399 0.2199 0.2549 0.076 Uiso calc R 1 . .
H H8C 0.4981 0.0463 0.2828 0.076 Uiso calc R 1 . .
C C9 0.2316(3) 0.1612(2) 0.25509(5) 0.0384(4) Uani d . 1 . .
C C10 0.1947(3) 0.1546(2) 0.21040(5) 0.0397(4) Uani d . 1 . .
H H10 0.3087 0.1449 0.1940 0.048 Uiso calc R 1 . .
C C11 -0.0069(3) 0.1616(2) 0.18819(5) 0.0386(4) Uani d . 1 . .
C C12 -0.0272(3) 0.1643(2) 0.13949(5) 0.0390(4) Uani d . 1 . .
C C13 0.1114(3) 0.0745(3) 0.11502(5) 0.0485(5) Uani d . 1 . .
H H13 0.2218 0.0086 0.1288 0.058 Uiso calc R 1 . .
C C14 0.0869(3) 0.0820(3) 0.07020(6) 0.0592(6) Uani d . 1 . .
H H14 0.1797 0.0195 0.0540 0.071 Uiso calc R 1 . .
C C15 -0.0728(4) 0.1807(3) 0.04946(6) 0.0612(6) Uani d . 1 . .
H H15 -0.0872 0.1869 0.0193 0.073 Uiso calc R 1 . .
C C16 -0.2117(4) 0.2703(3) 0.07320(6) 0.0621(6) Uani d . 1 . .
H H16 -0.3203 0.3375 0.0591 0.075 Uiso calc R 1 . .
C C17 -0.1908(3) 0.2612(3) 0.11809(6) 0.0525(5) Uani d . 1 . .
H H17 -0.2871 0.3205 0.1340 0.063 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'
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
C4 O1 C7 . . 117.43(15) ?
C9 N1 C1 . . 130.43(15) ?
C9 N1 H1 . . 114.8 ?
C1 N1 H1 . . 114.8 ?
C2 C1 C6 . . 118.82(15) ?
C2 C1 N1 . . 118.30(15) ?
C6 C1 N1 . . 122.79(15) ?
C1 C2 C3 . . 120.92(16) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 119.71(16) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
O1 C4 C5 . . 115.81(15) ?
O1 C4 C3 . . 124.58(16) ?
C5 C4 C3 . . 119.61(16) ?
C6 C5 C4 . . 120.56(17) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 120.36(17) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
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 ?
C9 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C9 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 120.13(16) ?
N1 C9 C8 . . 120.40(15) ?
C10 C9 C8 . . 119.40(15) ?
C9 C10 C11 . . 123.68(15) ?
C9 C10 H10 . . 118.2 ?
C11 C10 H10 . . 118.2 ?
O2 C11 C10 . . 123.41(16) ?
O2 C11 C12 . . 117.59(15) ?
C10 C11 C12 . . 118.94(14) ?
C13 C12 C17 . . 118.60(16) ?
C13 C12 C11 . . 122.58(16) ?
C17 C12 C11 . . 118.82(16) ?
C14 C13 C12 . . 120.45(18) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C15 C14 C13 . . 120.44(19) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 119.87(18) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.2(2) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C12 . . 120.42(18) ?
C16 C17 H17 . . 119.8 ?
C12 C17 H17 . . 119.8 ?
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
O1 C4 . 1.374(2) ?
O1 C7 . 1.413(2) ?
O2 C11 . 1.251(2) ?
N1 C9 . 1.333(2) ?
N1 C1 . 1.419(2) ?
N1 H1 . 0.86 ?
C1 C2 . 1.378(2) ?
C1 C6 . 1.385(2) ?
C2 C3 . 1.387(2) ?
C2 H2 . 0.93 ?
C3 C4 . 1.378(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.378(2) ?
C5 C6 . 1.377(2) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 C9 . 1.497(2) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C10 . 1.383(2) ?
C10 C11 . 1.415(2) ?
C10 H10 . 0.93 ?
C11 C12 . 1.500(2) ?
C12 C13 . 1.383(2) ?
C12 C17 . 1.387(3) ?
C13 C14 . 1.382(2) ?
C13 H13 . 0.93 ?
C14 C15 . 1.368(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.370(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.385(3) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
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
N1 H1 O2 . 0.86 1.91 2.629(2) 139
C8 H8B O2 1_655 0.96 2.49 3.351(3) 148
C3 H3 Cg2 2_455 0.93 2.84 3.712(3) 156
C13 H13 Cg1 2_545 0.93 2.82 3.619(3) 145
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
C9 N1 C1 C2 . . . . 142.48(19) ?
C9 N1 C1 C6 . . . . -40.9(3) ?
C6 C1 C2 C3 . . . . -0.9(3) ?
N1 C1 C2 C3 . . . . 175.86(16) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C7 O1 C4 C5 . . . . -167.8(2) ?
C7 O1 C4 C3 . . . . 12.2(3) ?
C2 C3 C4 O1 . . . . -179.76(17) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
O1 C4 C5 C6 . . . . 178.64(18) ?
C3 C4 C5 C6 . . . . -1.4(3) ?
C4 C5 C6 C1 . . . . 1.4(3) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
N1 C1 C6 C5 . . . . -176.83(17) ?
C1 N1 C9 C10 . . . . 178.77(16) ?
C1 N1 C9 C8 . . . . -4.1(3) ?
N1 C9 C10 C11 . . . . 2.1(3) ?
C8 C9 C10 C11 . . . . -175.06(16) ?
C9 C10 C11 O2 . . . . -0.6(3) ?
C9 C10 C11 C12 . . . . 176.46(16) ?
O2 C11 C12 C13 . . . . -149.89(18) ?
C10 C11 C12 C13 . . . . 32.8(2) ?
O2 C11 C12 C17 . . . . 30.3(2) ?
C10 C11 C12 C17 . . . . -146.95(18) ?
C17 C12 C13 C14 . . . . 0.2(3) ?
C11 C12 C13 C14 . . . . -179.60(17) ?
C12 C13 C14 C15 . . . . 1.0(3) ?
C13 C14 C15 C16 . . . . -1.1(3) ?
C14 C15 C16 C17 . . . . 0.0(3) ?
C15 C16 C17 C12 . . . . 1.2(3) ?
C13 C12 C17 C16 . . . . -1.3(3) ?
C11 C12 C17 C16 . . . . 178.51(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4667084
