#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/31/2103153.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_2103153
loop_
_publ_author_name
'Budzianowski, Armand'
'Katrusiak, Andrzej'
_publ_section_title
;
 Coupling of the lactone-ring conformation with crystal symmetry in
 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              125
_journal_page_last               133
_journal_paper_doi               10.1107/S0108768101017955
_journal_volume                  58
_journal_year                    2002
_chemical_formula_sum            'C14 H18 O3'
_chemical_formula_weight         234.28
_chemical_name_systematic
;
6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
;
_space_group_IT_number           14
_symmetry_cell_setting           P21/n
_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                 91.25(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.345(2)
_cell_length_b                   6.8530(10)
_cell_length_c                   13.973(3)
_cell_measurement_temperature    220.00(10)
_cell_volume                     1277.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220.00(10)
_diffrn_measured_fraction_theta_full .844
_diffrn_measured_fraction_theta_max .844
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0169
_diffrn_reflns_av_sigmaI/netI    .0843
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5221
_diffrn_reflns_theta_full        29.39
_diffrn_reflns_theta_max         29.39
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    .084
_exptl_crystal_colour            colourlees
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          .44
_exptl_crystal_size_mid          .38
_exptl_crystal_size_min          .19
_refine_diff_density_max         .379
_refine_diff_density_min         -.200
_refine_ls_extinction_coef       .0000(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   .996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .996
_refine_ls_R_factor_all          .0791
_refine_ls_R_factor_gt           .0550
_refine_ls_shift/su_max          .340
_refine_ls_shift/su_mean         .003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1526
_refine_ls_wR_factor_ref         .1707
_reflns_number_gt                1955
_reflns_number_total             2975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0046.cif
_cod_data_source_block           cum220
_cod_original_sg_symbol_H-M      monoclinic
_cod_database_code               2103153
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_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_occupancy
_atom_site_type_symbol
O1 .79818(7) .21076(17) -.30423(8) .0369(3) Uani d 1 O
O6 1.15996(8) .24937(16) -.48359(11) .0404(3) Uani d 1 O
H6 1.1576(18) .261(3) -.544(2) .064(7) Uiso d 1 H
O2 .70200(9) .2102(2) -.18045(10) .0594(4) Uani d 1 O
C2 .78373(12) .2462(2) -.21098(13) .0409(4) Uani d 1 C
C3 .87049(13) .3313(3) -.15758(14) .0476(5) Uani d 1 C
H3A .8550(16) .319(3) -.0897(19) .069(6) Uiso d 1 H
H3B .8739(13) .470(3) -.1760(14) .054(5) Uiso d 1 H
C4 .97048(12) .2307(2) -.18089(13) .0395(4) Uani d 1 C
C41 1.04961(17) .3449(5) -.12368(18) .0684(7) Uani d 1 C
H41A 1.0207(19) .367(4) -.062(2) .091(8) Uiso d 1 H
H41B 1.0631(13) .476(3) -.1514(14) .049(6) Uiso d 1 H
H41C 1.112(2) .275(4) -.121(2) .086(8) Uiso d 1 H
C42 .96690(19) .0159(4) -.14754(16) .0619(6) Uani d 1 C
H42A .9535(16) .004(4) -.0789(17) .076(7) Uiso d 1 H
H42B 1.0344(19) -.042(4) -.1539(17) .082(7) Uiso d 1 H
H42C .9081(18) -.065(3) -.1886(17) .077(7) Uiso d 1 H
C5 1.07157(10) .23537(19) -.33974(12) .0301(3) Uani d 1 C
C51 1.17397(12) .2134(3) -.29145(16) .0484(5) Uani d 1 C
H51A 1.2189(18) .159(3) -.3373(17) .072(6) Uiso d 1 H
H51B 1.1718(16) .117(3) -.2386(17) .069(7) Uiso d 1 H
H51C 1.1992(17) .332(4) -.2655(17) .068(6) Uiso d 1 H
C6 1.06879(10) .24643(18) -.43978(12) .0296(3) Uani d 1 C
C7 .97893(10) .25250(17) -.49408(11) .0278(3) Uani d 1 C
C71 .98267(14) .2598(2) -.60150(12) .0363(4) Uani d 1 C
H71A 1.0206(14) .153(3) -.6234(14) .058(6) Uiso d 1 H
H71B 1.0177(14) .377(3) -.6193(14) .060(6) Uiso d 1 H
H71C .918(2) .259(3) -.6340(19) .074(8) Uiso d 1 H
C8 .88888(10) .24588(18) -.44551(11) .0278(3) Uani d 1 C
C81 .78870(12) .2494(3) -.49783(14) .0389(4) Uani d 1 C
H81A .7822(17) .352(4) -.5422(18) .074(7) Uiso d 1 H
H81B .738(2) .267(4) -.449(2) .104(10) Uiso d 1 H
H81C .7775(17) .138(4) -.5313(18) .075(7) Uiso d 1 H
C9 .89247(10) .23684(19) -.34580(11) .0280(3) Uani d 1 C
C10 .98119(10) .23652(19) -.29019(11) .0295(3) Uani d 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C2 O1 C9 121.69(13)
O2 C2 O1 117.16(17)
O2 C2 C3 127.22(17)
O1 C2 C3 115.60(14)
C2 C3 C4 112.77(14)
C41 C4 C10 115.37(16)
C41 C4 C3 104.58(15)
C10 C4 C3 107.30(14)
C41 C4 C42 110.87(19)
C10 C4 C42 109.19(14)
C3 C4 C42 109.25(16)
C6 C5 C10 119.21(13)
C6 C5 C51 116.95(14)
C10 C5 C51 123.78(16)
O6 C6 C5 116.18(14)
O6 C6 C7 120.83(15)
C5 C6 C7 122.99(13)
C8 C7 C6 118.08(14)
C8 C7 C71 122.34(14)
C6 C7 C71 119.56(13)
C7 C8 C9 118.48(13)
C7 C8 C81 121.84(15)
C9 C8 C81 119.68(13)
C8 C9 C10 124.34(13)
C8 C9 O1 113.96(12)
C10 C9 O1 121.49(14)
C9 C10 C5 116.80(15)
C9 C10 C4 117.06(13)
C5 C10 C4 126.10(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.343(2)
O1 C9 1.4088(16)
O6 C6 1.3740(17)
O2 C2 1.205(2)
C2 C3 1.483(3)
C3 C4 1.543(2)
C4 C41 1.527(3)
C4 C10 1.538(2)
C4 C42 1.544(3)
C5 C6 1.400(2)
C5 C10 1.404(2)
C5 C51 1.518(2)
C6 C7 1.406(2)
C7 C8 1.3936(19)
C7 C71 1.504(2)
C8 C9 1.394(2)
C8 C81 1.510(2)
C9 C10 1.402(2)
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
C9 O1 C2 O2 -176.22(14)
C9 O1 C2 C3 5.4(2)
O2 C2 C3 C4 137.63(19)
O1 C2 C3 C4 -44.2(2)
C2 C3 C4 C41 177.12(19)
C2 C3 C4 C10 54.1(2)
C2 C3 C4 C42 -64.2(2)
C10 C5 C6 O6 178.48(12)
C51 C5 C6 O6 -4.21(19)
C10 C5 C6 C7 -2.1(2)
C51 C5 C6 C7 175.21(14)
O6 C6 C7 C8 178.97(12)
C5 C6 C7 C8 -.42(18)
O6 C6 C7 C71 .76(18)
C5 C6 C7 C71 -178.63(12)
C6 C7 C8 C9 1.04(18)
C71 C7 C8 C9 179.19(12)
C6 C7 C8 C81 -179.32(13)
C71 C7 C8 C81 -1.2(2)
C7 C8 C9 C10 .9(2)
C81 C8 C9 C10 -178.76(13)
C7 C8 C9 O1 -173.90(11)
C81 C8 C9 O1 6.46(18)
C2 O1 C9 C8 -163.41(13)
C2 O1 C9 C10 21.6(2)
C8 C9 C10 C5 -3.3(2)
O1 C9 C10 C5 171.07(12)
C8 C9 C10 C4 178.62(12)
O1 C9 C10 C4 -6.98(19)
C6 C5 C10 C9 3.79(19)
C51 C5 C10 C9 -173.32(14)
C6 C5 C10 C4 -178.36(12)
C51 C5 C10 C4 4.5(2)
C41 C4 C10 C9 -145.20(17)
C3 C4 C10 C9 -29.13(18)
C42 C4 C10 C9 89.17(17)
C41 C4 C10 C5 37.0(2)
C3 C4 C10 C5 153.03(15)
C42 C4 C10 C5 -88.67(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 535661
