#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230339.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_2230339
loop_
_publ_author_name
'Wang, Hui'
'He, Li-juan'
'Zheng, Wei-hua'
'Song, Hua-can'
_publ_section_title
;
 3-[(E)-1-(Benzyloxyimino)ethyl]-7-(3-methylbut-2-enyloxy)-2H-chromen-2-one
;
_journal_coeditor_code           HB5875
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1516
_journal_paper_doi               10.1107/S1600536811019015
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H23 N O4'
_chemical_formula_moiety         'C23 H23 N O4'
_chemical_formula_sum            'C23 H23 N O4'
_chemical_formula_weight         377.42
_chemical_name_systematic
;
3-[(E)-1-(Benzyloxyimino)ethyl]-7-(3-methylbut-2-enyloxy)-
2H-chromen-2-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           SHELXL-97
_cell_angle_alpha                92.368(3)
_cell_angle_beta                 92.067(3)
_cell_angle_gamma                102.340(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3038(19)
_cell_length_b                   11.467(3)
_cell_length_c                   12.184(3)
_cell_measurement_reflns_used    1391
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.41
_cell_volume                     995.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5604
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             430.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.185
_refine_ls_extinction_coef       0.049(5)
_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   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.1016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                2341
_reflns_number_total             3912
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5875.cif
_cod_data_source_block           I
_cod_original_cell_volume        995.0(5)
_cod_original_sg_symbol_Hall     ' -P 1'
_cod_database_code               2230339
_cod_database_fobs_code          2230339
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4410(2) 0.43803(16) 0.26381(14) 0.0548(5) Uani d . 1 1 . .
O O3 0.59306(19) 0.46642(13) 0.19438(12) 0.0611(4) Uani d . 1 1 . .
O O2 0.3010(2) 0.10766(13) 0.38943(12) 0.0622(4) Uani d . 1 1 . .
O O1 0.04470(18) 0.14660(12) 0.45666(10) 0.0492(4) Uani d . 1 1 . .
O O4 -0.50894(19) 0.21552(13) 0.61925(11) 0.0558(4) Uani d . 1 1 . .
C C19 0.9868(3) 0.6503(2) 0.19649(18) 0.0627(6) Uani d . 1 1 . .
H H19 0.9821 0.6483 0.2726 0.075 Uiso calc R 1 1 . .
C C18 1.1555(3) 0.6776(2) 0.1505(2) 0.0776(8) Uani d . 1 1 . .
H H18 1.2648 0.6934 0.1952 0.093 Uiso calc R 1 1 . .
C C17 1.1667(4) 0.6820(3) 0.0413(3) 0.0852(9) Uani d . 1 1 . .
H H17 1.2835 0.7011 0.0107 0.102 Uiso calc R 1 1 . .
C C16 1.0072(5) 0.6584(3) -0.0255(2) 0.0898(9) Uani d . 1 1 . .
H H16 1.0149 0.6616 -0.1014 0.108 Uiso calc R 1 1 . .
C C15 0.8327(4) 0.6296(2) 0.0215(2) 0.0743(7) Uani d . 1 1 . .
H H15 0.7235 0.6132 -0.0232 0.089 Uiso calc R 1 1 . .
C C14 0.8222(3) 0.62545(18) 0.13341(18) 0.0539(6) Uani d . 1 1 . .
C C13 0.6388(4) 0.5931(2) 0.1861(3) 0.0872(9) Uani d . 1 1 . .
H H13B 0.6471 0.6325 0.2587 0.105 Uiso calc R 1 1 . .
H H13A 0.5422 0.6184 0.1423 0.105 Uiso calc R 1 1 . .
C C11 0.3842(3) 0.32488(19) 0.26814(16) 0.0485(5) Uani d . 1 1 . .
C C12 0.4680(4) 0.2348(2) 0.2070(2) 0.0742(7) Uani d . 1 1 . .
H H12C 0.5063 0.2642 0.1369 0.111 Uiso calc R 1 1 . .
H H12A 0.3765 0.1611 0.1961 0.111 Uiso calc R 1 1 . .
H H12B 0.5750 0.2214 0.2486 0.111 Uiso calc R 1 1 . .
C C3 0.2208(3) 0.28938(17) 0.33767(15) 0.0449(5) Uani d . 1 1 . .
C C2 0.1984(3) 0.17731(18) 0.39329(15) 0.0462(5) Uani d . 1 1 . .
C C9 -0.0825(3) 0.21796(17) 0.47168(14) 0.0418(5) Uani d . 1 1 . .
C C4 0.0943(3) 0.35857(18) 0.35299(15) 0.0481(5) Uani d . 1 1 . .
H H4 0.1091 0.4300 0.3175 0.058 Uiso calc R 1 1 . .
C C10 -0.0610(3) 0.32596(17) 0.42160(15) 0.0437(5) Uani d . 1 1 . .
C C5 -0.1943(3) 0.39482(19) 0.44254(17) 0.0530(5) Uani d . 1 1 . .
H H5 -0.1839 0.4680 0.4104 0.064 Uiso calc R 1 1 . .
C C6 -0.3389(3) 0.35666(19) 0.50912(17) 0.0529(5) Uani d . 1 1 . .
H H6 -0.4246 0.4042 0.5231 0.064 Uiso calc R 1 1 . .
C C8 -0.2289(3) 0.17562(18) 0.53828(15) 0.0460(5) Uani d . 1 1 . .
H H8 -0.2400 0.1022 0.5699 0.055 Uiso calc R 1 1 . .
C C7 -0.3581(3) 0.24560(18) 0.55642(15) 0.0458(5) Uani d . 1 1 . .
C C20 -0.5503(3) 0.0961(2) 0.65844(17) 0.0564(6) Uani d . 1 1 . .
H H20B -0.4576 0.0878 0.7150 0.068 Uiso calc R 1 1 . .
H H20A -0.5481 0.0381 0.5985 0.068 Uiso calc R 1 1 . .
C C21 -0.7401(3) 0.07576(19) 0.70411(16) 0.0536(5) Uani d . 1 1 . .
H H21 -0.8390 0.0794 0.6550 0.064 Uiso calc R 1 1 . .
C C22 -0.7839(3) 0.05328(19) 0.80605(16) 0.0516(5) Uani d . 1 1 . .
C C24 -0.6452(4) 0.0473(3) 0.89720(19) 0.0908(9) Uani d . 1 1 . .
H H24C -0.5213 0.0617 0.8696 0.136 Uiso calc R 1 1 . .
H H24A -0.6738 -0.0304 0.9268 0.136 Uiso calc R 1 1 . .
H H24B -0.6510 0.1069 0.9539 0.136 Uiso calc R 1 1 . .
C C23 -0.9843(3) 0.0309(2) 0.8392(2) 0.0740(7) Uani d . 1 1 . .
H H23B -1.0643 0.0390 0.7770 0.111 Uiso calc R 1 1 . .
H H23C -0.9965 0.0879 0.8969 0.111 Uiso calc R 1 1 . .
H H23A -1.0200 -0.0484 0.8648 0.111 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 O3 . . 111.18(16) ?
N1 O3 C13 . . 108.13(15) ?
C9 O1 C2 . . 123.03(15) ?
C7 O4 C20 . . 117.49(15) ?
C18 C19 C14 . . 121.5(2) ?
C18 C19 H19 . . 119.2 ?
C14 C19 H19 . . 119.2 ?
C17 C18 C19 . . 120.6(3) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C18 C17 C16 . . 120.4(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C16 C15 . . 119.2(2) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C14 C15 C16 . . 120.1(2) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C15 C14 C19 . . 118.1(2) ?
C15 C14 C13 . . 121.5(2) ?
C19 C14 C13 . . 120.3(2) ?
O3 C13 C14 . . 108.12(18) ?
O3 C13 H13B . . 110.1 ?
C14 C13 H13B . . 110.1 ?
O3 C13 H13A . . 110.1 ?
C14 C13 H13A . . 110.1 ?
H13B C13 H13A . . 108.4 ?
N1 C11 C3 . . 113.69(18) ?
N1 C11 C12 . . 124.18(19) ?
C3 C11 C12 . . 122.1(2) ?
C11 C12 H12C . . 109.5 ?
C11 C12 H12A . . 109.5 ?
H12C C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12C C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C4 C3 C2 . . 118.98(17) ?
C4 C3 C11 . . 122.25(18) ?
C2 C3 C11 . . 118.75(17) ?
O2 C2 O1 . . 116.02(17) ?
O2 C2 C3 . . 126.66(18) ?
O1 C2 C3 . . 117.31(17) ?
O1 C9 C8 . . 116.41(16) ?
O1 C9 C10 . . 120.44(16) ?
C8 C9 C10 . . 123.15(18) ?
C3 C4 C10 . . 122.46(18) ?
C3 C4 H4 . . 118.8 ?
C10 C4 H4 . . 118.8 ?
C9 C10 C5 . . 117.12(17) ?
C9 C10 C4 . . 117.73(18) ?
C5 C10 C4 . . 125.15(18) ?
C6 C5 C10 . . 121.29(19) ?
C6 C5 H5 . . 119.4 ?
C10 C5 H5 . . 119.4 ?
C5 C6 C7 . . 119.89(19) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C7 C8 C9 . . 118.06(18) ?
C7 C8 H8 . . 121.0 ?
C9 C8 H8 . . 121.0 ?
O4 C7 C8 . . 124.63(18) ?
O4 C7 C6 . . 114.90(17) ?
C8 C7 C6 . . 120.47(18) ?
O4 C20 C21 . . 107.58(17) ?
O4 C20 H20B . . 110.2 ?
C21 C20 H20B . . 110.2 ?
O4 C20 H20A . . 110.2 ?
C21 C20 H20A . . 110.2 ?
H20B C20 H20A . . 108.5 ?
C22 C21 C20 . . 127.4(2) ?
C22 C21 H21 . . 116.3 ?
C20 C21 H21 . . 116.3 ?
C21 C22 C24 . . 124.4(2) ?
C21 C22 C23 . . 121.23(19) ?
C24 C22 C23 . . 114.42(18) ?
C22 C24 H24C . . 109.5 ?
C22 C24 H24A . . 109.5 ?
H24C C24 H24A . . 109.5 ?
C22 C24 H24B . . 109.5 ?
H24C C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C22 C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C22 C23 H23A . . 109.5 ?
H23B C23 H23A . . 109.5 ?
H23C C23 H23A . . 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
N1 C11 . 1.279(3) ?
N1 O3 . 1.4111(19) ?
O3 C13 . 1.428(3) ?
O2 C2 . 1.207(2) ?
O1 C9 . 1.375(2) ?
O1 C2 . 1.377(2) ?
O4 C7 . 1.356(2) ?
O4 C20 . 1.443(2) ?
C19 C18 . 1.353(3) ?
C19 C14 . 1.373(3) ?
C19 H19 . 0.9300 ?
C18 C17 . 1.338(3) ?
C18 H18 . 0.9300 ?
C17 C16 . 1.368(4) ?
C17 H17 . 0.9300 ?
C16 C15 . 1.396(4) ?
C16 H16 . 0.9300 ?
C15 C14 . 1.371(3) ?
C15 H15 . 0.9300 ?
C14 C13 . 1.488(3) ?
C13 H13B . 0.9700 ?
C13 H13A . 0.9700 ?
C11 C3 . 1.483(3) ?
C11 C12 . 1.495(3) ?
C12 H12C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C3 C4 . 1.354(3) ?
C3 C2 . 1.459(3) ?
C9 C8 . 1.382(2) ?
C9 C10 . 1.385(3) ?
C4 C10 . 1.428(3) ?
C4 H4 . 0.9300 ?
C10 C5 . 1.402(3) ?
C5 C6 . 1.363(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.401(3) ?
C6 H6 . 0.9300 ?
C8 C7 . 1.381(3) ?
C8 H8 . 0.9300 ?
C20 C21 . 1.488(3) ?
C20 H20B . 0.9700 ?
C20 H20A . 0.9700 ?
C21 C22 . 1.316(3) ?
C21 H21 . 0.9300 ?
C22 C24 . 1.490(3) ?
C22 C23 . 1.504(3) ?
C24 H24C . 0.9600 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C23 H23A . 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
C8 H8 O2 2_556 0.93 2.43 3.338(3) 167
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656706
