#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/95/2209508.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_2209508
loop_
_publ_author_name
'Lough, Alan J.'
'Villeneuve, Karine'
'Tam, William'
_publ_section_title
;
 Ethyl 2-acetonyl-3-(1H-isochromen-1-yl)acrylate
;
_journal_coeditor_code           HB2068
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2582
_journal_page_last               o2583
_journal_paper_doi               10.1107/S1600536806019751
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H18 O4'
_chemical_formula_moiety         'C17 H18 O4'
_chemical_formula_sum            'C17 H18 O4'
_chemical_formula_weight         286.31
_chemical_name_systematic
;
Ethyl 2-acetonyl-3-(1H-isochromen-1-yl)acrylate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6237(7)
_cell_length_b                   18.8830(12)
_cell_length_c                   8.4729(4)
_cell_measurement_reflns_used    17321
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1539.73(17)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL (Sheldrick, 2001)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7737
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing 1995)'
_exptl_crystal_colour            27.5
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       2.6
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.151
_refine_ls_extinction_coef       0.070(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0397
_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)+(0.0434P)²+0.2438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1567
_reflns_number_total             1857
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2068.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2209508
_cod_database_fobs_code          2209508
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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 0.22103(18) 0.67060(8) -0.1596(2) 0.0515(5) Uani d . 1 . .
O O2 0.72362(19) 0.65999(11) 0.2194(3) 0.0734(7) Uani d . 1 A .
O O3 0.5163(2) 0.69790(12) 0.3017(3) 0.0682(6) Uani d D 1 A 1
O O4 0.5694(2) 0.49536(9) 0.1604(2) 0.0538(5) Uani d . 1 . .
C C1 0.1086(3) 0.69576(15) -0.0767(3) 0.0562(7) Uani d . 1 . .
H H1A 0.0770 0.7423 -0.0996 0.067 Uiso calc R 1 . .
C C2 0.0416(3) 0.65938(14) 0.0330(4) 0.0544(7) Uani d . 1 . .
H H2A -0.0309 0.6811 0.0916 0.065 Uiso calc R 1 . .
C C3 0.0790(2) 0.58608(13) 0.0637(3) 0.0456(6) Uani d . 1 . .
C C4 -0.0049(3) 0.53905(16) 0.1480(3) 0.0549(7) Uani d . 1 . .
H H4A -0.0874 0.5557 0.1972 0.066 Uiso calc R 1 . .
C C5 0.0317(3) 0.46841(16) 0.1602(3) 0.0564(7) Uani d . 1 . .
H H5A -0.0258 0.4368 0.2180 0.068 Uiso calc R 1 . .
C C6 0.1516(3) 0.44342(14) 0.0886(4) 0.0538(6) Uani d . 1 . .
H H6A 0.1756 0.3948 0.0967 0.065 Uiso calc R 1 . .
C C7 0.2368(2) 0.48968(12) 0.0050(3) 0.0441(5) Uani d . 1 . .
H H7A 0.3187 0.4726 -0.0449 0.053 Uiso calc R 1 . .
C C8 0.2019(2) 0.56074(12) -0.0054(3) 0.0395(5) Uani d . 1 . .
C C9 0.2975(2) 0.61428(11) -0.0811(3) 0.0410(5) Uani d . 1 . .
H H9A 0.3572 0.5896 -0.1604 0.049 Uiso calc R 1 . .
C C10 0.3892(2) 0.64655(11) 0.0437(3) 0.0398(5) Uani d . 1 . .
H H10A 0.3477 0.6800 0.1128 0.048 Uiso calc R 1 . .
C C11 0.5236(2) 0.63228(11) 0.0659(3) 0.0400(5) Uani d . 1 A .
C C12 0.6098(2) 0.58315(11) -0.0346(3) 0.0422(5) Uani d . 1 . .
H H12A 0.7044 0.6031 -0.0459 0.051 Uiso calc R 1 . .
H H12B 0.5681 0.5803 -0.1412 0.051 Uiso calc R 1 . .
C C13 0.6203(2) 0.50943(11) 0.0337(3) 0.0402(5) Uani d . 1 . .
C C14 0.6945(3) 0.45530(13) -0.0636(3) 0.0526(6) Uani d . 1 . .
H H14A 0.7019 0.4110 -0.0038 0.079 Uiso calc R 1 . .
H H14B 0.7878 0.4726 -0.0895 0.079 Uiso calc R 1 . .
H H14C 0.6425 0.4468 -0.1612 0.079 Uiso calc R 1 . .
C C15 0.5995(3) 0.66428(13) 0.2008(4) 0.0510(6) Uani d . 1 . .
C C16 0.5950(6) 0.7384(4) 0.4218(7) 0.060(2) Uani d PD 0.598(10) A 1
H H16A 0.6481 0.7059 0.4909 0.072 Uiso calc PR 0.598(10) A 1
H H16B 0.6609 0.7714 0.3704 0.072 Uiso calc PR 0.598(10) A 1
C C17 0.4953(8) 0.7761(4) 0.5100(8) 0.094(3) Uani d PD 0.598(10) A 1
H H17A 0.5423 0.8050 0.5899 0.141 Uiso calc PR 0.598(10) A 1
H H17B 0.4324 0.7427 0.5619 0.141 Uiso calc PR 0.598(10) A 1
H H17C 0.4420 0.8070 0.4394 0.141 Uiso calc PR 0.598(10) A 1
C C16A 0.5572(14) 0.7149(6) 0.4663(7) 0.125(8) Uani d PD 0.402(10) A 2
H H16C 0.4789 0.7106 0.5415 0.150 Uiso calc PR 0.402(10) A 2
H H16D 0.6372 0.6865 0.5032 0.150 Uiso calc PR 0.402(10) A 2
C C17A 0.5929(14) 0.7858(8) 0.4349(16) 0.117(5) Uani d PD 0.402(10) A 2
H H17D 0.6261 0.8083 0.5321 0.176 Uiso calc PR 0.402(10) A 2
H H17E 0.5111 0.8112 0.3957 0.176 Uiso calc PR 0.402(10) A 2
H H17F 0.6666 0.7872 0.3550 0.176 Uiso calc PR 0.402(10) A 2
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'
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_publ_flag
C1 O1 C9 114.6(2) n
C15 O3 C16 112.3(3) ?
C2 C1 O1 124.3(2) ?
C2 C1 H1A 117.9 ?
O1 C1 H1A 117.9 ?
C1 C2 C3 119.9(2) ?
C1 C2 H2A 120.0 ?
C3 C2 H2A 120.0 ?
C4 C3 C8 118.9(2) ?
C4 C3 C2 123.6(2) ?
C8 C3 C2 117.3(2) ?
C5 C4 C3 120.2(2) ?
C5 C4 H4A 119.9 ?
C3 C4 H4A 119.9 ?
C4 C5 C6 120.5(2) ?
C4 C5 H5A 119.8 ?
C6 C5 H5A 119.8 ?
C5 C6 C7 120.0(2) ?
C5 C6 H6A 120.0 ?
C7 C6 H6A 120.0 ?
C8 C7 C6 119.8(2) ?
C8 C7 H7A 120.1 ?
C6 C7 H7A 120.1 ?
C7 C8 C3 120.5(2) ?
C7 C8 C9 121.83(19) ?
C3 C8 C9 117.5(2) ?
O1 C9 C10 108.78(17) ?
O1 C9 C8 112.08(17) ?
C10 C9 C8 109.26(19) ?
O1 C9 H9A 108.9 ?
C10 C9 H9A 108.9 ?
C8 C9 H9A 108.9 ?
C11 C10 C9 125.8(2) y
C11 C10 H10A 117.1 ?
C9 C10 H10A 117.1 ?
C10 C11 C15 120.2(2) ?
C10 C11 C12 125.3(2) ?
C15 C11 C12 114.52(19) ?
C11 C12 C13 112.76(19) ?
C11 C12 H12A 109.0 ?
C13 C12 H12A 109.0 ?
C11 C12 H12B 109.0 ?
C13 C12 H12B 109.0 ?
H12A C12 H12B 107.8 ?
O4 C13 C14 122.2(2) ?
O4 C13 C12 121.0(2) ?
C14 C13 C12 116.8(2) ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
O2 C15 O3 122.8(3) n
O2 C15 C11 124.0(3) n
O3 C15 C11 113.1(2) n
C17 C16 O3 106.1(5) ?
C17 C16 H16A 110.5 ?
O3 C16 H16A 110.5 ?
C17 C16 H16B 110.5 ?
O3 C16 H16B 110.5 ?
H16A C16 H16B 108.7 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C17A C16A H16C 112.7 ?
C17A C16A H16D 112.7 ?
H16C C16A H16D 110.2 ?
C16A C17A H17D 109.5 ?
C16A C17A H17E 109.5 ?
H17D C17A H17E 109.5 ?
C16A C17A H17F 109.5 ?
H17D C17A H17F 109.5 ?
H17E C17A H17F 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.323(4) n
C1 O1 1.375(3) y
C9 O1 1.454(3) y
O2 C15 1.208(3) ?
O3 C15 1.332(3) ?
O3 C16 1.481(5) ?
O4 C13 1.209(3) ?
C1 H1A 0.9500 ?
C2 C3 1.454(4) ?
C2 H2A 0.9500 ?
C3 C4 1.397(4) ?
C3 C8 1.403(3) ?
C4 C5 1.383(4) ?
C4 H4A 0.9500 ?
C5 C6 1.387(4) ?
C5 H5A 0.9500 ?
C6 C7 1.392(4) ?
C6 H6A 0.9500 ?
C7 C8 1.386(3) ?
C7 H7A 0.9500 ?
C8 C9 1.510(3) ?
C9 C10 1.506(3) ?
C9 H9A 1.0000 ?
C10 C11 1.335(3) n
C10 H10A 0.9500 ?
C11 C15 1.484(3) ?
C11 C12 1.508(3) ?
C12 C13 1.511(3) ?
C12 H12A 0.9900 ?
C12 H12B 0.9900 ?
C13 C14 1.495(3) ?
C14 H14A 0.9800 ?
C14 H14B 0.9800 ?
C14 H14C 0.9800 ?
C16 C17 1.409(7) ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C16A C17A 1.408(8) ?
C16A H16C 0.9900 ?
C16A H16D 0.9900 ?
C17A H17D 0.9800 ?
C17A H17E 0.9800 ?
C17A H17F 0.9800 ?
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
C9 H9A O4 2_664 1.00 2.32 3.275(3) 160
C12 H12B O4 2_664 0.99 2.57 3.442(3) 147
