#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/23/2232356.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_2232356
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chia, Tze Shyang'
'Narayana, B.'
'Nayak, Prakash S.'
'Sarojini, B. K.'
_publ_section_title
;
 (2E)-1-(2,5-Dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           IS2794
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3058
_journal_page_last               o3059
_journal_paper_doi               10.1107/S1600536811043224
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H15 N O5'
_chemical_formula_moiety         'C17 H15 N O5'
_chemical_formula_sum            'C17 H15 N O5'
_chemical_formula_weight         313.30
_chemical_name_systematic
;
(2E)-1-(2,5-Dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                86.5070(10)
_cell_angle_beta                 80.3420(10)
_cell_angle_gamma                76.3320(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5015(5)
_cell_length_b                   7.9962(5)
_cell_length_c                   13.2468(8)
_cell_measurement_reflns_used    5160
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.32
_cell_measurement_theta_min      2.62
_cell_volume                     760.96(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX DUO 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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16631
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0479
_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)+(0.1091P)²+0.0754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                3195
_reflns_number_total             4381
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2794.cif
_cod_data_source_block           I
_cod_database_code               2232356
_cod_database_fobs_code          2232356
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.15506(16) 0.16718(11) 0.39750(8) 0.0591(3) Uani d . 1 1
O O2 0.11277(18) -0.21224(13) 0.07147(7) 0.0671(3) Uani d . 1 1
O O3 0.3565(2) -0.36287(12) 0.39765(9) 0.0802(4) Uani d . 1 1
O O4 0.2174(3) 0.37169(16) 0.74170(13) 0.0989(5) Uani d . 1 1
O O5 0.3301(3) 0.3286(2) 0.88284(13) 0.1121(6) Uani d . 1 1
N N1 0.2941(2) 0.2780(2) 0.80490(12) 0.0729(4) Uani d . 1 1
C C1 0.14468(17) 0.07338(14) 0.31743(9) 0.0409(3) Uani d . 1 1
C C2 0.07436(19) 0.15014(15) 0.23001(10) 0.0487(3) Uani d . 1 1
H H2A 0.0312 0.2690 0.2265 0.058 Uiso calc R 1 1
C C3 0.0682(2) 0.05257(17) 0.14937(10) 0.0502(3) Uani d . 1 1
H H3A 0.0228 0.1057 0.0914 0.060 Uiso calc R 1 1
C C4 0.12955(19) -0.12516(16) 0.15424(9) 0.0458(3) Uani d . 1 1
C C5 0.19828(17) -0.20273(14) 0.23995(9) 0.0419(3) Uani d . 1 1
H H5A 0.2391 -0.3219 0.2429 0.050 Uiso calc R 1 1
C C6 0.20797(16) -0.10584(13) 0.32289(8) 0.0381(2) Uani d . 1 1
C C7 0.29087(19) -0.20926(14) 0.40881(9) 0.0452(3) Uani d . 1 1
C C8 0.2943(2) -0.12935(16) 0.50575(9) 0.0497(3) Uani d . 1 1
H H8A 0.2364 -0.0137 0.5148 0.060 Uiso calc R 1 1
C C9 0.37566(19) -0.21468(15) 0.57977(9) 0.0460(3) Uani d . 1 1
H H9A 0.4334 -0.3300 0.5689 0.055 Uiso calc R 1 1
C C10 0.38354(17) -0.14415(15) 0.67833(8) 0.0419(3) Uani d . 1 1
C C11 0.33505(18) 0.03198(16) 0.69527(9) 0.0455(3) Uani d . 1 1
H H11A 0.2967 0.1094 0.6436 0.055 Uiso calc R 1 1
C C12 0.34453(19) 0.09026(18) 0.78952(10) 0.0522(3) Uani d . 1 1
C C13 0.3995(2) -0.0188(2) 0.86864(11) 0.0644(4) Uani d . 1 1
H H13A 0.4044 0.0240 0.9316 0.077 Uiso calc R 1 1
C C14 0.4467(2) -0.1924(2) 0.85189(11) 0.0685(4) Uani d . 1 1
H H14A 0.4839 -0.2685 0.9044 0.082 Uiso calc R 1 1
C C15 0.4399(2) -0.25623(18) 0.75773(10) 0.0542(3) Uani d . 1 1
H H15A 0.4732 -0.3743 0.7476 0.065 Uiso calc R 1 1
C C16 0.0965(3) 0.34867(17) 0.39303(15) 0.0703(5) Uani d . 1 1
H H16A 0.1164 0.3956 0.4541 0.105 Uiso calc R 1 1
H H16B -0.0333 0.3808 0.3876 0.105 Uiso calc R 1 1
H H16C 0.1665 0.3928 0.3344 0.105 Uiso calc R 1 1
C C17 0.1863(3) -0.3918(2) 0.07001(13) 0.0749(5) Uani d . 1 1
H H17A 0.1741 -0.4357 0.0063 0.112 Uiso calc R 1 1
H H17B 0.1195 -0.4461 0.1256 0.112 Uiso calc R 1 1
H H17C 0.3152 -0.4158 0.0772 0.112 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'
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
C1 O1 C16 119.72(11)
C4 O2 C17 117.66(10)
O4 N1 O5 124.18(17)
O4 N1 C12 118.90(13)
O5 N1 C12 116.90(18)
O1 C1 C2 122.18(10)
O1 C1 C6 118.48(10)
C2 C1 C6 119.33(10)
C3 C2 C1 121.03(11)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C2 C3 C4 120.09(11)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
O2 C4 C5 124.45(11)
O2 C4 C3 115.96(10)
C5 C4 C3 119.58(10)
C4 C5 C6 121.45(10)
C4 C5 H5A 119.3
C6 C5 H5A 119.3
C1 C6 C5 118.51(10)
C1 C6 C7 126.70(9)
C5 C6 C7 114.78(9)
O3 C7 C8 119.73(10)
O3 C7 C6 118.73(10)
C8 C7 C6 121.54(10)
C9 C8 C7 122.75(11)
C9 C8 H8A 118.6
C7 C8 H8A 118.6
C8 C9 C10 125.75(11)
C8 C9 H9A 117.1
C10 C9 H9A 117.1
C11 C10 C15 118.74(11)
C11 C10 C9 121.88(10)
C15 C10 C9 119.38(11)
C12 C11 C10 119.18(12)
C12 C11 H11A 120.4
C10 C11 H11A 120.4
C13 C12 C11 122.74(13)
C13 C12 N1 119.30(13)
C11 C12 N1 117.96(13)
C14 C13 C12 118.00(12)
C14 C13 H13A 121.0
C12 C13 H13A 121.0
C13 C14 C15 121.00(13)
C13 C14 H14A 119.5
C15 C14 H14A 119.5
C14 C15 C10 120.34(13)
C14 C15 H15A 119.8
C10 C15 H15A 119.8
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3585(13)
O1 C16 1.4140(15)
O2 C4 1.3725(13)
O2 C17 1.4114(18)
O3 C7 1.2186(14)
O4 N1 1.214(2)
O5 N1 1.2241(18)
N1 C12 1.477(2)
C1 C2 1.4006(17)
C1 C6 1.4007(14)
C2 C3 1.3736(18)
C2 H2A 0.9300
C3 C4 1.3876(17)
C3 H3A 0.9300
C4 C5 1.3781(16)
C5 C6 1.4035(14)
C5 H5A 0.9300
C6 C7 1.4986(15)
C7 C8 1.4754(15)
C8 C9 1.3121(17)
C8 H8A 0.9300
C9 C10 1.4689(15)
C9 H9A 0.9300
C10 C11 1.3911(16)
C10 C15 1.3941(16)
C11 C12 1.3775(16)
C11 H11A 0.9300
C12 C13 1.375(2)
C13 C14 1.372(2)
C13 H13A 0.9300
C14 C15 1.3894(19)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
_geom_hbond_publ_flag
C3 H3A O2 2_555 0.9300 2.5500 3.4773(18) 172.00 yes
C8 H8A O1 . 0.9300 2.1200 2.7727(16) 126.00 yes
C17 H17A O5 1_544 0.9600 2.5000 3.309(2) 142.00 yes
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
C16 O1 C1 C2 -1.1(2)
C16 O1 C1 C6 178.45(13)
O1 C1 C2 C3 178.92(12)
C6 C1 C2 C3 -0.6(2)
C1 C2 C3 C4 1.0(2)
C17 O2 C4 C5 -6.0(2)
C17 O2 C4 C3 175.36(15)
C2 C3 C4 O2 178.06(13)
C2 C3 C4 C5 -0.6(2)
O2 C4 C5 C6 -178.65(12)
C3 C4 C5 C6 -0.1(2)
O1 C1 C6 C5 -179.64(11)
C2 C1 C6 C5 -0.08(18)
O1 C1 C6 C7 -0.96(19)
C2 C1 C6 C7 178.60(12)
C4 C5 C6 C1 0.41(19)
C4 C5 C6 C7 -178.42(12)
C1 C6 C7 O3 -172.69(14)
C5 C6 C7 O3 6.03(19)
C1 C6 C7 C8 7.4(2)
C5 C6 C7 C8 -173.92(12)
O3 C7 C8 C9 4.2(2)
C6 C7 C8 C9 -175.88(13)
C7 C8 C9 C10 -179.56(12)
C8 C9 C10 C11 -12.8(2)
C8 C9 C10 C15 166.73(14)
C15 C10 C11 C12 0.15(19)
C9 C10 C11 C12 179.72(12)
C10 C11 C12 C13 -0.3(2)
C10 C11 C12 N1 179.37(12)
O4 N1 C12 C13 -168.10(17)
O5 N1 C12 C13 10.5(2)
O4 N1 C12 C11 12.2(2)
O5 N1 C12 C11 -169.16(15)
C11 C12 C13 C14 0.1(2)
N1 C12 C13 C14 -179.54(15)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 C10 -0.4(2)
C11 C10 C15 C14 0.2(2)
C9 C10 C15 C14 -179.40(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5833540
