#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/20/2212016.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_2212016
loop_
_publ_author_name
'Gardiner, Michael G.'
'Jones, Roderick C.'
'Mason, Celina M.'
'Smith, Jason A.'
_publ_section_title
(RS)-2-(3,4-Methylenedioxyphenyl)-5-phenyl-3,6-dihydro-2H-pyran
_journal_coeditor_code           BH2073
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o955
_journal_page_last               o957
_journal_paper_doi               10.1107/S1600536807003194
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H16 O3'
_chemical_formula_moiety         'C18 H16 O3'
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_chemical_melting_point          .425E-305
_chemical_name_systematic
;
(RS)-2-(3,4-Methylenedioxyphenyl)-5-phenyl-3,6-dihydro-2H-pyran
;
_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                81.24(5)
_cell_angle_beta                 80.21(2)
_cell_angle_gamma                82.05(4)
_cell_formula_units_Z            2
_cell_length_a                   6.6380(13)
_cell_length_b                   7.911(10)
_cell_length_c                   13.498(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15.66
_cell_measurement_theta_min      9.82
_cell_volume                     685.7(9)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'X-SEED (Barbour, 2001) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2750
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0442
_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)+(0.0716P)²+0.1555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                1932
_reflns_number_total             2413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2073.cif
_cod_data_source_block           I
_cod_database_code               2212016
_cod_database_fobs_code          2212016
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
O O1 0.12451(18) 0.76062(18) -0.00835(9) 0.0472(4) Uani d . 1
O O2 -0.3421(2) 0.43061(19) 0.26385(10) 0.0561(4) Uani d . 1
O O3 -0.2820(2) 0.47454(18) 0.42096(9) 0.0501(4) Uani d . 1
C C1 0.2124(3) 0.8621(3) -0.09679(13) 0.0433(4) Uani d . 1
H H1A 0.1673 0.9826 -0.0911 0.052 Uiso calc R 1
H H1B 0.1623 0.8341 -0.1551 0.052 Uiso calc R 1
C C2 0.4443(2) 0.8350(2) -0.11424(12) 0.0330(4) Uani d . 1
C C3 0.5435(3) 0.7648(2) -0.03782(13) 0.0389(4) Uani d . 1
H H3 0.6865 0.7487 -0.0497 0.047 Uiso calc R 1
C C4 0.4361(3) 0.7101(2) 0.06656(13) 0.0390(4) Uani d . 1
H H4A 0.5010 0.7514 0.1160 0.047 Uiso calc R 1
H H4B 0.4487 0.5854 0.0797 0.047 Uiso calc R 1
C C5 0.2089(3) 0.7812(2) 0.07803(13) 0.0374(4) Uani d . 1
H H5 0.1986 0.9047 0.0824 0.045 Uiso calc R 1
C C6 0.5468(2) 0.8896(2) -0.21797(12) 0.0329(4) Uani d . 1
C C7 0.7398(3) 0.8116(2) -0.25646(14) 0.0441(4) Uani d . 1
H H7 0.8083 0.7255 -0.2152 0.053 Uiso calc R 1
C C8 0.8311(3) 0.8596(3) -0.35456(15) 0.0511(5) Uani d . 1
H H8 0.9599 0.8059 -0.3786 0.061 Uiso calc R 1
C C9 0.7324(3) 0.9872(2) -0.41739(14) 0.0471(5) Uani d . 1
H H9 0.7942 1.0198 -0.4835 0.057 Uiso calc R 1
C C10 0.5415(3) 1.0654(2) -0.38087(13) 0.0424(4) Uani d . 1
H H10 0.4742 1.1513 -0.4227 0.051 Uiso calc R 1
C C11 0.4492(3) 1.0180(2) -0.28316(13) 0.0372(4) Uani d . 1
H H11 0.3199 1.0720 -0.2600 0.045 Uiso calc R 1
C C12 0.0809(2) 0.6982(2) 0.17137(13) 0.0347(4) Uani d . 1
C C13 -0.0727(3) 0.5973(2) 0.16350(12) 0.0358(4) Uani d . 1
H H13 -0.0968 0.5759 0.1009 0.043 Uiso calc R 1
C C14 -0.1849(3) 0.5323(2) 0.25207(13) 0.0351(4) Uani d . 1
C C15 -0.1496(3) 0.5585(2) 0.34539(12) 0.0364(4) Uani d . 1
C C16 0.0009(3) 0.6542(3) 0.35537(14) 0.0470(5) Uani d . 1
H H16 0.0259 0.6712 0.4187 0.056 Uiso calc R 1
C C17 0.1148(3) 0.7246(3) 0.26592(14) 0.0455(5) Uani d . 1
H H17 0.2170 0.7916 0.2699 0.055 Uiso calc R 1
C C18 -0.4219(3) 0.4145(3) 0.36833(14) 0.0529(5) Uani d . 1
H H18A -0.4387 0.2950 0.3938 0.063 Uiso calc R 1
H H18B -0.5555 0.4820 0.3790 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'
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
C5 O1 C1 111.78(14) yes
C14 O2 C18 105.40(14) ?
C15 O3 C18 104.49(13) ?
O1 C1 C2 113.01(14) yes
O1 C1 H1A 109.0 ?
C2 C1 H1A 109.0 ?
O1 C1 H1B 109.0 ?
C2 C1 H1B 109.0 ?
H1A C1 H1B 107.8 ?
C3 C2 C6 124.15(15) yes
C3 C2 C1 119.37(15) yes
C6 C2 C1 116.48(14) yes
C2 C3 C4 123.14(16) yes
C2 C3 H3 118.4 ?
C4 C3 H3 118.4 ?
C3 C4 C5 110.94(14) yes
C3 C4 H4A 109.5 ?
C5 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
C5 C4 H4B 109.5 ?
H4A C4 H4B 108.0 ?
O1 C5 C12 108.62(14) yes
O1 C5 C4 110.16(14) yes
C12 C5 C4 113.69(14) yes
O1 C5 H5 108.1 ?
C12 C5 H5 108.1 ?
C4 C5 H5 108.1 ?
C7 C6 C11 117.30(16) ?
C7 C6 C2 121.72(15) ?
C11 C6 C2 120.93(15) ?
C8 C7 C6 121.23(17) ?
C8 C7 H7 119.4 ?
C6 C7 H7 119.4 ?
C7 C8 C9 120.49(18) ?
C7 C8 H8 119.8 ?
C9 C8 H8 119.8 ?
C10 C9 C8 119.15(17) ?
C10 C9 H9 120.4 ?
C8 C9 H9 120.4 ?
C11 C10 C9 120.73(17) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C6 121.10(16) ?
C10 C11 H11 119.4 ?
C6 C11 H11 119.4 ?
C17 C12 C13 119.90(16) ?
C17 C12 C5 118.96(15) ?
C13 C12 C5 121.13(15) ?
C14 C13 C12 116.84(16) ?
C14 C13 H13 121.6 ?
C12 C13 H13 121.6 ?
C13 C14 C15 122.82(16) ?
C13 C14 O2 127.56(16) ?
C15 C14 O2 109.60(15) ?
C16 C15 C14 121.57(16) ?
C16 C15 O3 128.26(16) ?
C14 C15 O3 110.16(15) ?
C15 C16 C17 116.61(17) ?
C15 C16 H16 121.7 ?
C17 C16 H16 121.7 ?
C12 C17 C16 122.24(17) ?
C12 C17 H17 118.9 ?
C16 C17 H17 118.9 ?
O2 C18 O3 108.62(15) ?
O2 C18 H18A 110.0 ?
O3 C18 H18A 110.0 ?
O2 C18 H18B 110.0 ?
O3 C18 H18B 110.0 ?
H18A C18 H18B 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.416(2) yes
O1 C1 1.418(2) yes
O2 C14 1.377(2) ?
O2 C18 1.413(2) ?
O3 C15 1.380(2) ?
O3 C18 1.429(2) ?
C1 C2 1.508(2) yes
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C3 1.327(2) yes
C2 C6 1.477(2) yes
C3 C4 1.496(2) yes
C3 H3 0.9300 ?
C4 C5 1.525(2) yes
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C12 1.509(2) ?
C5 H5 0.9800 ?
C6 C7 1.395(2) ?
C6 C11 1.402(3) ?
C7 C8 1.379(3) ?
C7 H7 0.9300 ?
C8 C9 1.383(3) ?
C8 H8 0.9300 ?
C9 C10 1.377(3) ?
C9 H9 0.9300 ?
C10 C11 1.376(2) ?
C10 H10 0.9300 ?
C11 H11 0.9300 ?
C12 C17 1.384(3) ?
C12 C13 1.405(2) ?
C13 C14 1.365(2) ?
C13 H13 0.9300 ?
C14 C15 1.370(2) ?
C15 C16 1.369(3) ?
C16 C17 1.393(3) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
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
_geom_torsion_publ_flag
C5 O1 C1 C2 52.1(2) yes
O1 C1 C2 C3 -18.6(2) yes
O1 C1 C2 C6 161.16(15) ?
C6 C2 C3 C4 -179.84(16) ?
C1 C2 C3 C4 -0.1(3) yes
C2 C3 C4 C5 -12.5(2) yes
C1 O1 C5 C12 169.10(13) ?
C1 O1 C5 C4 -65.77(19) yes
C3 C4 C5 O1 44.0(2) yes
C3 C4 C5 C12 166.21(15) ?
C3 C2 C6 C7 27.5(3) yes
C1 C2 C6 C7 -152.24(17) ?
C3 C2 C6 C11 -155.07(17) yes
C1 C2 C6 C11 25.2(2) ?
C11 C6 C7 C8 0.3(3) ?
C2 C6 C7 C8 177.82(17) ?
C6 C7 C8 C9 0.0(3) ?
C7 C8 C9 C10 -0.2(3) ?
C8 C9 C10 C11 0.0(3) ?
C9 C10 C11 C6 0.3(3) ?
C7 C6 C11 C10 -0.5(2) ?
C2 C6 C11 C10 -177.99(16) ?
O1 C5 C12 C17 -170.23(16) ?
C4 C5 C12 C17 66.7(2) ?
O1 C5 C12 C13 8.9(2) ?
C4 C5 C12 C13 -114.15(19) ?
C17 C12 C13 C14 1.2(2) ?
C5 C12 C13 C14 -177.91(15) ?
C12 C13 C14 C15 -1.5(3) ?
C12 C13 C14 O2 -179.89(16) ?
C18 O2 C14 C13 -173.58(18) ?
C18 O2 C14 C15 7.9(2) ?
C13 C14 C15 C16 0.7(3) ?
O2 C14 C15 C16 179.28(16) ?
C13 C14 C15 O3 -178.46(15) ?
O2 C14 C15 O3 0.2(2) ?
C18 O3 C15 C16 172.9(2) ?
C18 O3 C15 C14 -8.0(2) ?
C14 C15 C16 C17 0.6(3) ?
O3 C15 C16 C17 179.53(17) ?
C13 C12 C17 C16 0.0(3) ?
C5 C12 C17 C16 179.13(17) ?
C15 C16 C17 C12 -0.9(3) ?
C14 O2 C18 O3 -12.9(2) ?
C15 O3 C18 O2 12.9(2) ?
