#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/31/2103150.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_2103150
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           11
_symmetry_cell_setting           P21/m
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 94.36(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7560(10)
_cell_length_b                   6.9470(10)
_cell_length_c                   9.575(2)
_cell_measurement_temperature    328(2)
_cell_volume                     647.07(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      328(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0222
_diffrn_reflns_av_sigmaI/netI    .0146
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            955
_diffrn_reflns_theta_full        55.07
_diffrn_reflns_theta_max         55.07
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    .675
_exptl_crystal_colour            colourlees
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .12
_refine_diff_density_max         .205
_refine_diff_density_min         -.236
_refine_ls_extinction_coef       .045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.317
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.317
_refine_ls_R_factor_all          .0646
_refine_ls_R_factor_gt           .0551
_refine_ls_shift/su_max          1.155
_refine_ls_shift/su_mean         .017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.1455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1518
_refine_ls_wR_factor_ref         .1606
_reflns_number_gt                742
_reflns_number_total             899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0046.cif
_cod_data_source_block           a329
_cod_original_sg_symbol_H-M      monoclinic
_cod_database_code               2103150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 .1034(2) .2500 .4959(3) .0726(10) Uani d S 1 O
O2 -.1143(3) .2500 .5229(4) .1117(15) Uani d S 1 O
O6 .6494(3) .2500 .6762(3) .0656(9) Uani d S 1 O
H6 .711(7) .2500 .621(6) .13(2) Uiso d S 1 H
C2 -.0001(4) .2500 .5738(5) .0727(13) Uani d S 1 C
C3 .0384(5) .3567(10) .7110(6) .0790(19) Uani d P .50 C
H3A -.050(7) .350(9) .778(7) .12(2) Uiso d P .50 H
H3B .092(4) .525(6) .738(4) .034(10) Uiso d P .50 H
C4 .1626(4) .2500 .7909(4) .0699(13) Uani d S 1 C
C41 .1909(8) .3884(17) .9172(7) .114(3) Uani d P .50 C
H41A .2176 .5173 .8868 .03(4) Uiso d P .25 H
H41B .2735 .3429 .9782 .08(4) Uiso d P .25 H
H41C .1178 .3996 .9752 .027(18) Uiso d P .25 H
H41D .1883 .3226 1.0067 .15(7) Uiso d P .25 H
H41E .1324 .4970 .9153 2(4) Uiso d P .25 H
H41F .2881 .4403 .9183 .19(8) Uiso d P .25 H
C42 .1260(10) .0488(13) .8271(11) .103(2) Uiso d P .50 C
H42A .0560 .0561 .8935 .09(4) Uiso d P .25 H
H42B .2083 -.0072 .8775 .11(11) Uiso d P .25 H
H42C .0991 -.0196 .7489 2(5) Uiso d P .25 H
H42D .1863 -.0365 .7865 2(5) Uiso d P .25 H
H42E .0340 .0267 .8024 .4(2) Uiso d P .25 H
H42F .1431 .0391 .9310 .08(4) Uiso d P .25 H
C5 .4201(3) .2500 .7319(3) .0485(9) Uani d S 1 C
C51 .4805(6) .2500 .8829(5) .0858(17) Uani d S 1 C
H51A .554(10) .2500 .890(9) .20(4) Uiso d S 1 H
H51C .439(4) .146(6) .939(4) .143(16) Uiso d . 1 H
C6 .5136(3) .2500 .6287(4) .0455(9) Uani d S 1 C
C7 .4730(3) .2500 .4858(3) .0430(9) Uani d S 1 C
C71 .5796(4) .2500 .3806(5) .0592(12) Uani d S 1 C
H71A .535(6) .2500 .291(6) .12(2) Uiso d S 1 H
H71B .641(3) .150(5) .393(3) .098(11) Uiso d . 1 H
C8 .3335(3) .2500 .4449(3) .0443(9) Uani d S 1 C
C81 .2805(5) .2500 .2940(4) .0601(12) Uani d S 1 C
H81A .189(8) .2500 .287(6) .033(17) Uiso d SP .50 H
H81C .306(4) .124(7) .241(5) .037(11) Uiso d P .50 H
H81D .340(10) .2500 .250(10) .07(3) Uiso d SP .50 H
H81E .215(6) .135(8) .258(5) .063(14) Uiso d P .50 H
C9 .2416(3) .2500 .5493(3) .0445(9) Uani d S 1 C
C10 .2791(3) .2500 .6916(3) .0478(10) Uani d S 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 .0181 .0091 '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 .0492 .0322 '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
C2 O1 C9 . . 123.8(3)
C6 O6 H6 . . 121(4)
O2 C2 O1 . . 120.8(4)
O2 C2 C3 . . 121.1(3)
O1 C2 C3 . . 110.0(3)
O2 C2 C3 . 4_565 121.1(3)
O1 C2 C3 . 4_565 110.0(3)
C3 C2 C3 . 4_565 58.0(5)
C3 C3 C42 4_565 4_565 115.9(5)
C3 C3 C2 4_565 . 61.0(3)
C42 C3 C2 4_565 . 159.5(5)
C3 C3 C4 4_565 . 61.8(3)
C42 C3 C4 4_565 . 58.0(4)
C2 C3 C4 . . 108.6(4)
C3 C3 H3A 4_565 . 88(3)
C42 C3 H3A 4_565 . 91(3)
C2 C3 H3A . . 109(3)
C4 C3 H3A . . 108(3)
C3 C3 H3B 4_565 . 154.4(18)
C42 C3 H3B 4_565 . 42.5(18)
C2 C3 H3B . . 132(2)
C4 C3 H3B . . 92.7(19)
H3A C3 H3B . . 104(4)
C42 C4 C42 4_565 . 139.5(7)
C42 C4 C10 4_565 . 110.2(4)
C42 C4 C10 . . 110.2(4)
C42 C4 C3 4_565 4_565 111.6(5)
C42 C4 C3 . 4_565 58.7(5)
C10 C4 C3 . 4_565 106.2(3)
C42 C4 C3 4_565 . 58.7(5)
C42 C4 C3 . . 111.6(5)
C10 C4 C3 . . 106.2(3)
C3 C4 C3 4_565 . 56.4(6)
C42 C4 C41 4_565 . 43.1(5)
C42 C4 C41 . . 115.5(6)
C10 C4 C41 . . 112.7(4)
C3 C4 C41 4_565 . 139.2(4)
C3 C4 C41 . . 99.9(4)
C42 C4 C41 4_565 4_565 115.5(6)
C42 C4 C41 . 4_565 43.1(5)
C10 C4 C41 . 4_565 112.7(4)
C3 C4 C41 4_565 4_565 99.9(4)
C3 C4 C41 . 4_565 139.2(4)
C41 C4 C41 . 4_565 76.5(8)
C42 C41 C4 4_565 . 65.4(6)
C42 C41 C41 4_565 4_565 113.0(7)
C4 C41 C41 . 4_565 51.8(4)
C42 C41 H41A 4_565 . 64.1(8)
C4 C41 H41A . . 111.6(6)
C41 C41 H41A 4_565 . 155.7(4)
C42 C41 H41B 4_565 . 161.4(10)
C4 C41 H41B . . 110.1(7)
C41 C41 H41B 4_565 . 71.8(6)
H41A C41 H41B . . 103.8(9)
C42 C41 H41C 4_565 . 90.8(8)
C4 C41 H41C . . 114.4(8)
C41 C41 H41C 4_565 . 94.8(7)
H41A C41 H41C . . 109.2(9)
H41B C41 H41C . . 107.0(7)
C42 C41 H41D 4_565 . 144.2(10)
C4 C41 H41D . . 112.3(9)
C41 C41 H41D 4_565 . 62.0(6)
H41A C41 H41D . . 135.6(9)
H41B C41 H41D . . 54.3(5)
H41C C41 H41D . . 56.5(5)
C42 C41 H41E 4_565 . 50.8(7)
C4 C41 H41E . . 114.0(7)
C41 C41 H41E 4_565 . 143.0(6)
H41A C41 H41E . . 56.0(6)
H41B C41 H41E . . 135.7(9)
H41C C41 H41E . . 57.4(4)
H41D C41 H41E . . 109.7(6)
C42 C41 H41F 4_565 . 110.0(11)
C4 C41 H41F . . 109.8(5)
C41 C41 H41F 4_565 . 110.8(6)
H41A C41 H41F . . 53.9(6)
H41B C41 H41F . . 53.1(4)
H41C C41 H41F . . 135.7(9)
H41D C41 H41F . . 104.2(7)
H41E C41 H41F . . 106.2(11)
C41 C42 C4 4_565 . 71.5(8)
C41 C42 C3 4_565 4_565 131.1(10)
C4 C42 C3 . 4_565 63.3(5)
C41 C42 H42A 4_565 . 81.9(9)
C4 C42 H42A . . 107.2(7)
C3 C42 H42A 4_565 . 94.1(7)
C41 C42 H42B 4_565 . 52.0(8)
C4 C42 H42B . . 106.5(8)
C3 C42 H42B 4_565 . 158.9(9)
H42A C42 H42B . . 106.7(9)
C41 C42 H42C 4_565 . 161.9(12)
C4 C42 H42C . . 111.0(8)
C3 C42 H42C 4_565 . 60.4(6)
H42A C42 H42C . . 113.2(10)
H42B C42 H42C . . 111.8(9)
C41 C42 H42D 4_565 . 103.3(11)
C4 C42 H42D . . 109.1(7)
C3 C42 H42D 4_565 . 108.0(9)
H42A C42 H42D . . 143.0(10)
H42B C42 H42D . . 56.1(5)
H42C C42 H42D . . 58.6(6)
C41 C42 H42E 4_565 . 138.0(11)
C4 C42 H42E . . 109.9(8)
C3 C42 H42E 4_565 . 52.8(5)
H42A C42 H42E . . 57.1(5)
H42B C42 H42E . . 143.1(10)
H42C C42 H42E . . 59.2(7)
H42D C42 H42E . . 114.6(11)
C41 C42 H42F 4_565 . 38.4(5)
C4 C42 H42F . . 105.7(8)
C3 C42 H42F 4_565 . 144.1(9)
H42A C42 H42F . . 54.7(5)
H42B C42 H42F . . 54.3(6)
H42C C42 H42F . . 143.3(10)
H42D C42 H42F . . 108.0(9)
H42E C42 H42F . . 109.2(9)
C6 C5 C10 . . 119.1(3)
C6 C5 C51 . . 116.6(4)
C10 C5 C51 . . 124.3(4)
C5 C51 H51A . . 114(7)
C5 C51 H51C . . 112(2)
H51A C51 H51C . . 113(5)
O6 C6 C5 . . 115.7(3)
O6 C6 C7 . . 121.5(3)
C5 C6 C7 . . 122.9(3)
C8 C7 C6 . . 118.4(3)
C8 C7 C71 . . 121.7(3)
C6 C7 C71 . . 119.9(3)
C7 C71 H71A . . 109(3)
C7 C71 H71B . . 113.0(19)
H71A C71 H71B . . 112(3)
C7 C8 C9 . . 118.0(3)
C7 C8 C81 . . 122.2(3)
C9 C8 C81 . . 119.9(3)
C8 C81 H81A . . 110(4)
C8 C81 H81C . . 113(2)
H81A C81 H81C . . 104(3)
C8 C81 H81D . . 108(7)
H81A C81 H81D . . 142(8)
H81C C81 H81D . . 60(3)
C8 C81 H81E . . 118(3)
H81A C81 H81E . . 53(3)
H81C C81 H81E . . 52(3)
H81D C81 H81E . . 107(6)
C10 C9 C8 . . 124.7(3)
C10 C9 O1 . . 122.2(3)
C8 C9 O1 . . 113.0(3)
C9 C10 C5 . . 116.9(3)
C9 C10 C4 . . 117.2(3)
C5 C10 C4 . . 126.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.300(4)
O1 C9 . 1.405(4)
O2 C2 . 1.182(5)
O6 C6 . 1.367(4)
O6 H6 . .83(6)
C2 C3 . 1.530(7)
C2 C3 4_565 1.530(7)
C3 C3 4_565 1.483(15)
C3 C42 4_565 1.501(12)
C3 C4 . 1.569(7)
C3 H3A . 1.12(7)
C3 H3B . 1.30(4)
C4 C42 4_565 1.490(9)
C4 C42 . 1.490(9)
C4 C10 . 1.537(5)
C4 C3 4_565 1.569(7)
C4 C41 . 1.554(9)
C4 C41 4_565 1.554(9)
C41 C42 4_565 1.119(12)
C41 C41 4_565 1.92(2)
C41 H41A . .983(12)
C41 H41B . 1.009(8)
C41 H41C . .940(7)
C41 H41D . .973(9)
C41 H41E . .945(9)
C41 H41F . 1.014(9)
C42 C41 4_565 1.119(12)
C42 C3 4_565 1.501(12)
C42 H42A . .969(9)
C42 H42B . .984(10)
C42 H42C . .908(11)
C42 H42D . .939(9)
C42 H42E . .924(10)
C42 H42F . .999(10)
C5 C6 . 1.394(5)
C5 C10 . 1.400(5)
C5 C51 . 1.519(5)
C51 H51A . .72(10)
C51 H51C . 1.00(4)
C6 C7 . 1.395(5)
C7 C8 . 1.387(4)
C7 C71 . 1.503(5)
C71 H71A . .93(6)
C71 H71B . .92(3)
C8 C9 . 1.393(4)
C8 C81 . 1.498(5)
C81 H81A . .89(7)
C81 H81C . 1.05(5)
C81 H81D . .74(10)
C81 H81E . 1.06(6)
C9 C10 . 1.384(5)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C9 O1 C2 O2 . . 180.0
C9 O1 C2 C3 . . 31.0(3)
C9 O1 C2 C3 . 4_565 -31.0(3)
O2 C2 C3 C3 . 4_565 109.5(3)
O1 C2 C3 C3 . 4_565 -101.6(2)
O2 C2 C3 C42 . 4_565 -163.6(17)
O1 C2 C3 C42 . 4_565 -14.7(19)
C3 C2 C3 C42 4_565 4_565 87.0(19)
O2 C2 C3 C4 . . 150.3(3)
O1 C2 C3 C4 . . -60.8(4)
C3 C2 C3 C4 4_565 . 40.8(4)
C3 C3 C4 C42 4_565 4_565 -156.9(4)
C2 C3 C4 C42 . 4_565 162.7(6)
C3 C3 C4 C42 4_565 . -21.1(4)
C42 C3 C4 C42 4_565 . 135.8(8)
C2 C3 C4 C42 . . -61.6(6)
C3 C3 C4 C10 4_565 . 98.9(2)
C42 C3 C4 C10 4_565 . -104.2(4)
C2 C3 C4 C10 . . 58.5(4)
C42 C3 C4 C3 4_565 4_565 156.9(4)
C2 C3 C4 C3 . 4_565 -40.4(4)
C3 C3 C4 C41 4_565 . -143.8(4)
C42 C3 C4 C41 4_565 . 13.1(6)
C2 C3 C4 C41 . . 175.8(5)
C3 C3 C4 C41 4_565 4_565 -63.0(7)
C42 C3 C4 C41 4_565 4_565 93.9(9)
C2 C3 C4 C41 . 4_565 -103.5(8)
C42 C4 C41 C42 . 4_565 -136.3(10)
C10 C4 C41 C42 . 4_565 95.8(6)
C3 C4 C41 C42 4_565 4_565 -65.4(10)
C3 C4 C41 C42 . 4_565 -16.5(7)
C41 C4 C41 C42 4_565 4_565 -155.0(6)
C42 C4 C41 C41 4_565 4_565 155.0(6)
C42 C4 C41 C41 . 4_565 18.7(5)
C10 C4 C41 C41 . 4_565 -109.2(4)
C3 C4 C41 C41 4_565 4_565 89.5(7)
C3 C4 C41 C41 . 4_565 138.5(4)
C42 C4 C42 C41 4_565 4_565 -73.7(15)
C10 C4 C42 C41 . 4_565 102.0(7)
C3 C4 C42 C41 4_565 4_565 -160.9(8)
C3 C4 C42 C41 . 4_565 -140.3(6)
C41 C4 C42 C41 . 4_565 -27.1(7)
C42 C4 C42 C3 4_565 4_565 87.2(13)
C10 C4 C42 C3 . 4_565 -97.1(4)
C3 C4 C42 C3 . 4_565 20.6(5)
C41 C4 C42 C3 . 4_565 133.8(5)
C41 C4 C42 C3 4_565 4_565 160.9(8)
C10 C5 C6 O6 . . 180.0
C51 C5 C6 O6 . . .0
C10 C5 C6 C7 . . .0
C51 C5 C6 C7 . . 180.0
O6 C6 C7 C8 . . 180.0
C5 C6 C7 C8 . . .0
O6 C6 C7 C71 . . .0
C5 C6 C7 C71 . . 180.0
C6 C7 C8 C9 . . .0
C71 C7 C8 C9 . . 180.0
C6 C7 C8 C81 . . 180.0
C71 C7 C8 C81 . . .0
C7 C8 C9 C10 . . .0
C81 C8 C9 C10 . . 180.0
C7 C8 C9 O1 . . 180.0
C81 C8 C9 O1 . . .0
C2 O1 C9 C10 . . .0
C2 O1 C9 C8 . . 180.0
C8 C9 C10 C5 . . .0
O1 C9 C10 C5 . . 180.0
C8 C9 C10 C4 . . 180.0
O1 C9 C10 C4 . . .0
C6 C5 C10 C9 . . .0
C51 C5 C10 C9 . . 180.0
C6 C5 C10 C4 . . 180.0
C51 C5 C10 C4 . . .0000(10)
C42 C4 C10 C9 4_565 . -91.5(5)
C42 C4 C10 C9 . . 91.5(5)
C3 C4 C10 C9 4_565 . 29.5(3)
C3 C4 C10 C9 . . -29.5(3)
C41 C4 C10 C9 . . -137.9(4)
C41 C4 C10 C9 4_565 . 137.9(4)
C42 C4 C10 C5 4_565 . 88.5(5)
C42 C4 C10 C5 . . -88.5(5)
C3 C4 C10 C5 4_565 . -150.5(3)
C3 C4 C10 C5 . . 150.5(3)
C41 C4 C10 C5 . . 42.1(4)
C41 C4 C10 C5 4_565 . -42.1(4)
