#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/31/2103148.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_2103148
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                 94.39(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.753(2)
_cell_length_b                   6.9330(10)
_cell_length_c                   9.572(2)
_cell_measurement_temperature    306(2)
_cell_volume                     645.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      306(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_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  .0263
_diffrn_reflns_av_sigmaI/netI    .0150
_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            1106
_diffrn_reflns_theta_full        60.10
_diffrn_reflns_theta_max         60.10
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    .676
_exptl_crystal_colour            colourlees
_exptl_crystal_density_diffrn    1.206
_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         .161
_refine_diff_density_min         -.135
_refine_ls_extinction_coef       .048(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   .930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .930
_refine_ls_R_factor_all          .0556
_refine_ls_R_factor_gt           .0468
_refine_ls_shift/su_max          1.111
_refine_ls_shift/su_mean         .021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.5550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1029
_refine_ls_wR_factor_ref         .1094
_reflns_number_gt                864
_reflns_number_total             1045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0046.cif
_cod_data_source_block           a308
_cod_original_sg_symbol_H-M      monoclinic
_cod_database_code               2103148
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 .10337(19) .2500 .4954(2) .0704(8) Uani d S 1 O
O2 -.1147(2) .2500 .5232(3) .1068(12) Uani d S 1 O
O6 .6497(2) .2500 .6764(3) .0645(7) Uani d S 1 O
H6 .703(5) .2500 .607(5) .122(19) Uiso d S 1 H
C2 -.0006(3) .2500 .5743(4) .0713(11) Uani d S 1 C
C3 .0381(5) .3542(10) .7114(5) .0729(16) Uani d P .50 C
H3A -.046(5) .336(7) .759(5) .083(16) Uiso d P .50 H
H3B .073(5) .513(7) .696(6) .064(16) Uiso d P .50 H
C4 .1627(3) .2500 .7908(4) .0685(11) Uani d S 1 C
C41 .1953(9) .3885(18) .9212(7) .121(4) Uani d P .50 C
H41A .2178 .5175 .8869 .08(9) Uiso d P .25 H
H41B .2735 .3426 .9783 .04(2) Uiso d P .25 H
H41C .1178 .3998 .9751 .08(3) Uiso d P .25 H
H41D .1882 .3224 1.0066 .17(7) Uiso d P .25 H
H41E .1326 .4974 .9153 .21(16) Uiso d P .25 H
H41F .2883 .4402 .9184 .38(19) Uiso d P .25 H
C42 .1284(8) .0503(16) .8300(13) .117(3) Uani d P .50 C
H42A .0555 .0555 .8933 .05(2) Uiso d P .25 H
H42B .2077 -.0082 .8775 .05(8) Uiso d P .25 H
H42C .0986 -.0203 .7488 .20(18) Uiso d P .25 H
H42D .1858 -.0375 .7864 2.0(18) Uiso d P .25 H
H42E .0335 .0262 .8022 .13(5) Uiso d P .25 H
H42F .1426 .0383 .9310 .15(13) Uiso d P .25 H
C5 .4203(3) .2500 .7319(3) .0467(8) Uani d S 1 C
C51 .4810(5) .2500 .8820(5) .0834(14) Uani d S 1 C
H51A .582(8) .2500 .878(7) .22(3) Uiso d S 1 H
H51C .458(4) .149(6) .932(4) .163(18) Uiso d . 1 H
C6 .5129(3) .2500 .6283(3) .0448(8) Uani d S 1 C
C7 .4731(3) .2500 .4859(3) .0430(7) Uani d S 1 C
C71 .5798(4) .2500 .3803(4) .0584(10) Uani d S 1 C
H71A .544(4) .2500 .286(5) .102(15) Uiso d S 1 H
H71B .642(3) .141(4) .392(3) .104(10) Uiso d . 1 H
C8 .3331(3) .2500 .4446(3) .0428(7) Uani d S 1 C
C81 .2809(4) .2500 .2929(4) .0597(10) Uani d S 1 C
H81A .192(5) .2500 .278(5) .13(2) Uiso d S 1 H
H81C .306(3) .139(5) .238(3) .125(12) Uiso d . 1 H
C9 .2418(3) .2500 .5493(3) .0435(7) Uani d S 1 C
C10 .2789(3) .2500 .6912(3) .0460(8) 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 . . 123.4(3)
C6 O6 H6 . . 111(3)
O2 C2 O1 . . 120.5(4)
O2 C2 C3 . . 121.5(3)
O1 C2 C3 . . 110.2(3)
O2 C2 C3 . 4_565 121.5(3)
O1 C2 C3 . 4_565 110.2(3)
C3 C2 C3 . 4_565 56.8(5)
C3 C3 C2 4_565 . 61.6(3)
C3 C3 C42 4_565 4_565 115.6(6)
C2 C3 C42 . 4_565 159.3(4)
C3 C3 C4 4_565 . 62.4(3)
C2 C3 C4 . . 109.5(4)
C42 C3 C4 4_565 . 57.1(5)
C3 C3 H3A 4_565 . 82(3)
C2 C3 H3A . . 100(3)
C42 C3 H3A 4_565 . 100(3)
C4 C3 H3A . . 111(3)
C3 C3 H3B 4_565 . 161(2)
C2 C3 H3B . . 113(3)
C42 C3 H3B 4_565 . 62(3)
C4 C3 H3B . . 106(3)
H3A C3 H3B . . 117(4)
C42 C4 C42 . 4_565 138.7(8)
C42 C4 C10 . . 110.4(4)
C42 C4 C10 4_565 . 110.4(4)
C42 C4 C3 . 4_565 60.5(6)
C42 C4 C3 4_565 4_565 112.0(5)
C10 C4 C3 . 4_565 106.4(3)
C42 C4 C3 . . 112.0(5)
C42 C4 C3 4_565 . 60.5(6)
C10 C4 C3 . . 106.4(3)
C3 C4 C3 4_565 . 55.1(5)
C42 C4 C41 . . 113.7(7)
C42 C4 C41 4_565 . 43.1(6)
C10 C4 C41 . . 112.0(4)
C3 C4 C41 4_565 . 139.8(4)
C3 C4 C41 . . 101.8(4)
C42 C4 C41 . 4_565 43.1(6)
C42 C4 C41 4_565 4_565 113.7(7)
C10 C4 C41 . 4_565 112.0(4)
C3 C4 C41 4_565 4_565 101.8(4)
C3 C4 C41 . 4_565 139.8(4)
C41 C4 C41 . 4_565 74.5(9)
C42 C41 C4 4_565 . 63.4(6)
C42 C41 C41 4_565 4_565 112.1(9)
C4 C41 C41 . 4_565 52.8(4)
C42 C41 H41A 4_565 . 62.1(8)
C4 C41 H41A . . 108.9(6)
C41 C41 H41A 4_565 . 155.5(4)
C42 C41 H41B 4_565 . 162.1(11)
C4 C41 H41B . . 110.5(8)
C41 C41 H41B 4_565 . 70.6(8)
H41A C41 H41B . . 107.7(11)
C42 C41 H41C 4_565 . 87.3(8)
C4 C41 H41C . . 111.0(9)
C41 C41 H41C 4_565 . 94.7(8)
H41A C41 H41C . . 108.2(10)
H41B C41 H41C . . 110.4(8)
C42 C41 H41D 4_565 . 140.7(12)
C4 C41 H41D . . 111.4(11)
C41 C41 H41D 4_565 . 61.0(7)
H41A C41 H41D . . 139.7(10)
H41B C41 H41D . . 56.8(5)
H41C C41 H41D . . 57.0(5)
C42 C41 H41E 4_565 . 48.7(6)
C4 C41 H41E . . 109.7(7)
C41 C41 H41E 4_565 . 141.1(7)
H41A C41 H41E . . 55.2(7)
H41B C41 H41E . . 139.6(11)
H41C C41 H41E . . 56.2(4)
H41D C41 H41E . . 109.9(7)
C42 C41 H41F 4_565 . 108.8(12)
C4 C41 H41F . . 109.3(5)
C41 C41 H41F 4_565 . 111.5(6)
H41A C41 H41F . . 55.0(7)
H41B C41 H41F . . 55.8(5)
H41C C41 H41F . . 139.7(11)
H41D C41 H41F . . 109.3(8)
H41E C41 H41F . . 107.2(13)
C41 C42 C4 4_565 . 73.5(10)
C41 C42 C3 4_565 4_565 132.3(13)
C4 C42 C3 . 4_565 62.4(4)
C41 C42 H42A 4_565 . 84.9(12)
C4 C42 H42A . . 108.3(9)
C3 C42 H42A 4_565 . 92.2(6)
C41 C42 H42B 4_565 . 52.8(9)
C4 C42 H42B . . 109.1(10)
C3 C42 H42B 4_565 . 158.9(8)
H42A C42 H42B . . 108.9(9)
C41 C42 H42C 4_565 . 162.1(11)
C4 C42 H42C . . 109.7(7)
C3 C42 H42C 4_565 . 59.4(6)
H42A C42 H42C . . 109.8(11)
H42B C42 H42C . . 111.0(11)
C41 C42 H42D 4_565 . 104.9(10)
C4 C42 H42D . . 109.8(5)
C3 C42 H42D 4_565 . 106.1(10)
H42A C42 H42D . . 141.9(11)
H42B C42 H42D . . 56.8(4)
H42C C42 H42D . . 57.2(8)
C41 C42 H42E 4_565 . 140.1(13)
C4 C42 H42E . . 109.0(6)
C3 C42 H42E 4_565 . 51.8(5)
H42A C42 H42E . . 56.0(4)
H42B C42 H42E . . 141.9(10)
H42C C42 H42E . . 56.8(8)
H42D C42 H42E . . 110.9(16)
C41 C42 H42F 4_565 . 39.9(6)
C4 C42 H42F . . 108.4(12)
C3 C42 H42F 4_565 . 143.6(8)
H42A C42 H42F . . 55.6(6)
H42B C42 H42F . . 56.1(6)
H42C C42 H42F . . 141.9(11)
H42D C42 H42F . . 110.0(8)
H42E C42 H42F . . 108.9(6)
C6 C5 C10 . . 118.7(3)
C6 C5 C51 . . 116.7(3)
C10 C5 C51 . . 124.7(3)
C5 C51 H51A . . 106(4)
C5 C51 H51C . . 114(2)
H51A C51 H51C . . 109(3)
O6 C6 C7 . . 121.2(3)
O6 C6 C5 . . 115.3(3)
C7 C6 C5 . . 123.5(2)
C6 C7 C8 . . 118.2(3)
C6 C7 C71 . . 120.3(3)
C8 C7 C71 . . 121.5(3)
C7 C71 H71A . . 114(3)
C7 C71 H71B . . 112.6(17)
H71A C71 H71B . . 107(2)
C9 C8 C7 . . 117.6(3)
C9 C8 C81 . . 120.6(3)
C7 C8 C81 . . 121.8(3)
C8 C81 H81A . . 115(3)
C8 C81 H81C . . 115.9(18)
H81A C81 H81C . . 102(3)
C10 C9 C8 . . 125.2(2)
C10 C9 O1 . . 122.2(2)
C8 C9 O1 . . 112.6(2)
C9 C10 C5 . . 116.8(3)
C9 C10 C4 . . 117.5(3)
C5 C10 C4 . . 125.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.311(4)
O1 C9 . 1.409(3)
O2 C2 . 1.180(4)
O6 C6 . 1.378(3)
O6 H6 . .88(5)
C2 C3 . 1.520(6)
C2 C3 4_565 1.520(6)
C3 C3 4_565 1.445(13)
C3 C42 4_565 1.534(11)
C3 C4 . 1.561(6)
C3 H3A . .97(5)
C3 H3B . 1.16(5)
C4 C42 . 1.480(10)
C4 C42 4_565 1.480(10)
C4 C10 . 1.536(4)
C4 C3 4_565 1.561(6)
C4 C41 . 1.587(10)
C4 C41 4_565 1.587(10)
C41 C42 4_565 1.131(15)
C41 C41 4_565 1.92(3)
C41 H41A . .984(13)
C41 H41B . .958(8)
C41 H41C . .951(8)
C41 H41D . .945(10)
C41 H41E . .971(10)
C41 H41F . .977(11)
C42 C41 4_565 1.131(15)
C42 C3 4_565 1.534(11)
C42 H42A . .970(7)
C42 H42B . .957(9)
C42 H42C . .946(16)
C42 H42D . .945(10)
C42 H42E . .958(11)
C42 H42F . .969(12)
C5 C6 . 1.391(4)
C5 C10 . 1.403(4)
C5 C51 . 1.512(5)
C51 H51A . .99(8)
C51 H51C . .88(4)
C6 C7 . 1.388(4)
C7 C8 . 1.392(4)
C7 C71 . 1.505(4)
C71 H71A . .94(4)
C71 H71B . .97(3)
C8 C9 . 1.390(4)
C8 C81 . 1.502(4)
C81 H81A . .87(5)
C81 H81C . .97(3)
C9 C10 . 1.379(4)
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 . . 30.4(3)
C9 O1 C2 C3 . 4_565 -30.4(3)
O2 C2 C3 C3 . 4_565 109.3(3)
O1 C2 C3 C3 . 4_565 -101.5(2)
O2 C2 C3 C42 . 4_565 -163.0(19)
O1 C2 C3 C42 . 4_565 -14(2)
C3 C2 C3 C42 4_565 4_565 88(2)
O2 C2 C3 C4 . . 150.8(3)
O1 C2 C3 C4 . . -60.0(4)
C3 C2 C3 C4 4_565 . 41.5(4)
C3 C3 C4 C42 4_565 . -21.9(5)
C2 C3 C4 C42 . . -63.0(7)
C42 C3 C4 C42 4_565 . 134.7(10)
C3 C3 C4 C42 4_565 4_565 -156.6(5)
C2 C3 C4 C42 . 4_565 162.3(6)
C3 C3 C4 C10 4_565 . 98.83(18)
C2 C3 C4 C10 . . 57.7(4)
C42 C3 C4 C10 4_565 . -104.6(5)
C2 C3 C4 C3 . 4_565 -41.1(4)
C42 C3 C4 C3 4_565 4_565 156.6(5)
C3 C3 C4 C41 4_565 . -143.7(5)
C2 C3 C4 C41 . . 175.1(5)
C42 C3 C4 C41 4_565 . 12.9(7)
C3 C3 C4 C41 4_565 4_565 -63.9(7)
C2 C3 C4 C41 . 4_565 -105.1(8)
C42 C3 C4 C41 4_565 4_565 92.7(9)
C42 C4 C41 C42 . 4_565 -137.1(8)
C10 C4 C41 C42 . 4_565 96.8(6)
C3 C4 C41 C42 4_565 4_565 -65.3(11)
C3 C4 C41 C42 . 4_565 -16.5(8)
C41 C4 C41 C42 4_565 4_565 -155.3(5)
C42 C4 C41 C41 . 4_565 18.2(4)
C42 C4 C41 C41 4_565 4_565 155.3(5)
C10 C4 C41 C41 . 4_565 -107.9(4)
C3 C4 C41 C41 4_565 4_565 90.0(7)
C3 C4 C41 C41 . 4_565 138.8(4)
C42 C4 C42 C41 4_565 4_565 -71.0(15)
C10 C4 C42 C41 . 4_565 100.8(8)
C3 C4 C42 C41 4_565 4_565 -161.4(9)
C3 C4 C42 C41 . 4_565 -140.8(7)
C41 C4 C42 C41 . 4_565 -26.1(7)
C42 C4 C42 C3 4_565 4_565 90.4(15)
C10 C4 C42 C3 . 4_565 -97.8(4)
C3 C4 C42 C3 . 4_565 20.6(5)
C41 C4 C42 C3 . 4_565 135.3(5)
C41 C4 C42 C3 4_565 4_565 161.4(9)
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 . . .0
C42 C4 C10 C9 . . 92.9(6)
C42 C4 C10 C9 4_565 . -92.9(6)
C3 C4 C10 C9 4_565 . 28.8(3)
C3 C4 C10 C9 . . -28.8(3)
C41 C4 C10 C9 . . -139.3(4)
C41 C4 C10 C9 4_565 . 139.3(4)
C42 C4 C10 C5 . . -87.1(6)
C42 C4 C10 C5 4_565 . 87.1(6)
C3 C4 C10 C5 4_565 . -151.2(3)
C3 C4 C10 C5 . . 151.2(3)
C41 C4 C10 C5 . . 40.7(4)
C41 C4 C10 C5 4_565 . -40.7(4)
