#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/31/2103149.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_2103149
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                 94.380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7530(10)
_cell_length_b                   6.9410(10)
_cell_length_c                   9.5730(10)
_cell_measurement_temperature    317(2)
_cell_volume                     646.16(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      317(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  .0314
_diffrn_reflns_av_sigmaI/netI    .0151
_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            1035
_diffrn_reflns_theta_full        57.51
_diffrn_reflns_theta_max         57.51
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    .675
_exptl_crystal_colour            colourlees
_exptl_crystal_density_diffrn    1.204
_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         .187
_refine_diff_density_min         -.164
_refine_ls_extinction_coef       .047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          .0531
_refine_ls_R_factor_gt           .0442
_refine_ls_shift/su_max          .407
_refine_ls_shift/su_mean         .003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0815P)²+0.1245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1246
_refine_ls_wR_factor_ref         .1342
_reflns_number_gt                804
_reflns_number_total             975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0046.cif
_cod_data_source_block           a319
_cod_original_sg_symbol_H-M      monoclinic
_cod_database_code               2103149
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 .10325(17) .2500 .4956(2) .0706(7) Uani d S 1 O
O2 -.1145(2) .2500 .5232(3) .1082(11) Uani d S 1 O
O6 .64967(18) .2500 .6761(2) .0645(7) Uani d S 1 O
H6 .711(4) .2500 .609(4) .102(13) Uiso d S 1 H
C2 -.0004(3) .2500 .5741(3) .0713(10) Uani d S 1 C
C3 .0382(4) .3550(8) .7120(5) .0736(13) Uani d P .50 C
H3A -.047(5) .331(6) .762(5) .095(16) Uiso d P .50 H
H3B .069(4) .507(6) .699(5) .063(12) Uiso d P .50 H
C4 .1624(3) .2500 .7907(3) .0684(9) Uani d S 1 C
C41 .1955(8) .3891(15) .9212(6) .120(3) Uani d P .50 C
H41A .2178 .5171 .8874 .08(9) Uiso d P .25 H
H41B .2735 .3421 .9784 .040(17) Uiso d P .25 H
H41C .1178 .3993 .9754 .06(2) Uiso d P .25 H
H41D .1882 .3219 1.0068 .14(5) Uiso d P .25 H
H41E .1326 .4969 .9157 .27(16) Uiso d P .25 H
H41F .2883 .4397 .9187 .38(18) Uiso d P .25 H
C42 .1270(6) .0495(13) .8282(10) .116(3) Uani d P .50 C
H42A .0552 .0551 .8925 .034(15) Uiso d P .25 H
H42B .2075 -.0084 .8767 .07(8) Uiso d P .25 H
H42C .0986 -.0199 .7478 .4(2) Uiso d P .25 H
H42D .1856 -.0372 .7855 2(2) Uiso d P .25 H
H42E .0333 .0263 .8013 .10(4) Uiso d P .25 H
H42F .1423 .0377 .9302 .09(4) Uiso d P .25 H
C5 .4203(2) .2500 .7319(3) .0478(7) Uani d S 1 C
C51 .4816(4) .2500 .8819(4) .0834(12) Uani d S 1 C
H51A .578(7) .2500 .870(6) .19(3) Uiso d S 1 H
H51C .448(3) .153(5) .933(3) .147(14) Uiso d . 1 H
C6 .5132(2) .2500 .6289(3) .0444(7) Uani d S 1 C
C7 .4731(2) .2500 .4857(3) .0438(7) Uani d S 1 C
C71 .5796(3) .2500 .3804(4) .0579(8) Uani d S 1 C
H71A .541(4) .2500 .288(5) .111(14) Uiso d S 1 H
H71B .642(3) .146(4) .394(2) .098(8) Uiso d . 1 H
C8 .3329(2) .2500 .4446(2) .0434(7) Uani d S 1 C
C81 .2807(3) .2500 .2932(3) .0595(9) Uani d S 1 C
H81A .176(7) .2500 .293(6) .057(16) Uiso d SP .50 H
H81C .314(4) .128(6) .240(4) .050(9) Uiso d P .50 H
H81D .351(10) .2500 .222(9) .12(3) Uiso d SP .50 H
H81E .217(4) .142(7) .266(4) .061(11) Uiso d P .50 H
C9 .2418(2) .2500 .5487(3) .0438(7) Uani d S 1 C
C10 .2790(2) .2500 .6918(2) .0462(7) 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 . . 123.9(2)
C6 O6 H6 . . 116(3)
O2 C2 O1 . . 120.7(3)
O2 C2 C3 . . 121.2(2)
O1 C2 C3 . . 110.3(2)
O2 C2 C3 . 4_565 121.2(2)
O1 C2 C3 . 4_565 110.3(2)
C3 C2 C3 . 4_565 56.9(4)
C3 C3 C42 4_565 4_565 116.0(5)
C3 C3 C2 4_565 . 61.5(2)
C42 C3 C2 4_565 . 159.1(3)
C3 C3 C4 4_565 . 62.1(2)
C42 C3 C4 4_565 . 57.9(4)
C2 C3 C4 . . 109.0(3)
C3 C3 H3A 4_565 . 80(3)
C42 C3 H3A 4_565 . 100(3)
C2 C3 H3A . . 100(3)
C4 C3 H3A . . 110(3)
C3 C3 H3B 4_565 . 162.4(19)
C42 C3 H3B 4_565 . 61(2)
C2 C3 H3B . . 114(2)
C4 C3 H3B . . 107(2)
H3A C3 H3B . . 117(3)
C42 C4 C42 4_565 . 139.3(6)
C42 C4 C10 4_565 . 110.2(3)
C42 C4 C10 . . 110.2(3)
C42 C4 C3 4_565 4_565 111.7(4)
C42 C4 C3 . 4_565 59.5(4)
C10 C4 C3 . 4_565 106.7(2)
C42 C4 C3 4_565 . 59.5(4)
C42 C4 C3 . . 111.7(4)
C10 C4 C3 . . 106.7(2)
C3 C4 C3 4_565 . 55.8(4)
C42 C4 C41 4_565 . 43.8(5)
C42 C4 C41 . . 114.6(6)
C10 C4 C41 . . 111.6(3)
C3 C4 C41 4_565 . 140.0(4)
C3 C4 C41 . . 101.5(3)
C42 C4 C41 4_565 4_565 114.6(6)
C42 C4 C41 . 4_565 43.8(5)
C10 C4 C41 . 4_565 111.6(3)
C3 C4 C41 4_565 4_565 101.5(3)
C3 C4 C41 . 4_565 140.0(4)
C41 C4 C41 . 4_565 74.6(7)
C42 C41 C4 4_565 . 63.1(5)
C42 C41 C41 4_565 4_565 111.7(7)
C4 C41 C41 . 4_565 52.7(3)
C42 C41 H41A 4_565 . 62.5(6)
C4 C41 H41A . . 109.1(4)
C41 C41 H41A 4_565 . 155.5(3)
C42 C41 H41B 4_565 . 162.4(8)
C4 C41 H41B . . 110.2(6)
C41 C41 H41B 4_565 . 70.1(6)
H41A C41 H41B . . 108.2(9)
C42 C41 H41C 4_565 . 87.4(6)
C4 C41 H41C . . 110.5(8)
C41 C41 H41C 4_565 . 94.2(6)
H41A C41 H41C . . 108.7(8)
H41B C41 H41C . . 110.1(6)
C42 C41 H41D 4_565 . 140.4(10)
C4 C41 H41D . . 110.7(9)
C41 C41 H41D 4_565 . 60.6(5)
H41A C41 H41D . . 140.1(8)
H41B C41 H41D . . 56.6(4)
H41C C41 H41D . . 56.8(4)
C42 C41 H41E 4_565 . 49.0(4)
C4 C41 H41E . . 109.7(5)
C41 C41 H41E 4_565 . 140.7(6)
H41A C41 H41E . . 55.6(5)
H41B C41 H41E . . 140.1(9)
H41C C41 H41E . . 56.2(3)
H41D C41 H41E . . 109.8(5)
C42 C41 H41F 4_565 . 109.4(9)
C4 C41 H41F . . 109.4(4)
C41 C41 H41F 4_565 . 111.1(5)
H41A C41 H41F . . 55.4(6)
H41B C41 H41F . . 55.9(4)
H41C C41 H41F . . 140.1(9)
H41D C41 H41F . . 109.3(7)
H41E C41 H41F . . 107.9(10)
C41 C42 C4 4_565 . 73.1(8)
C41 C42 C3 4_565 4_565 132.3(10)
C4 C42 C3 . 4_565 62.7(3)
C41 C42 H42A 4_565 . 84.2(9)
C4 C42 H42A . . 108.0(7)
C3 C42 H42A 4_565 . 92.8(5)
C41 C42 H42B 4_565 . 51.9(7)
C4 C42 H42B . . 108.1(7)
C3 C42 H42B 4_565 . 159.1(6)
H42A C42 H42B . . 108.1(7)
C41 C42 H42C 4_565 . 161.3(9)
C4 C42 H42C . . 110.2(5)
C3 C42 H42C 4_565 . 60.0(5)
H42A C42 H42C . . 111.2(8)
H42B C42 H42C . . 111.2(9)
C41 C42 H42D 4_565 . 103.6(8)
C4 C42 H42D . . 109.5(4)
C3 C42 H42D 4_565 . 107.1(8)
H42A C42 H42D . . 142.4(8)
H42B C42 H42D . . 56.5(3)
H42C C42 H42D . . 57.7(6)
C41 C42 H42E 4_565 . 139.9(10)
C4 C42 H42E . . 109.4(5)
C3 C42 H42E 4_565 . 52.0(4)
H42A C42 H42E . . 56.5(3)
H42B C42 H42E . . 142.4(8)
H42C C42 H42E . . 57.7(6)
H42D C42 H42E . . 112.3(12)
C41 C42 H42F 4_565 . 39.3(5)
C4 C42 H42F . . 107.4(9)
C3 C42 H42F 4_565 . 143.6(7)
H42A C42 H42F . . 55.4(4)
H42B C42 H42F . . 55.3(5)
H42C C42 H42F . . 142.5(8)
H42D C42 H42F . . 109.1(6)
H42E C42 H42F . . 109.1(5)
C6 C5 C10 . . 119.1(2)
C6 C5 C51 . . 116.2(3)
C10 C5 C51 . . 124.6(3)
C5 C51 H51A . . 102(4)
C5 C51 H51C . . 112(2)
H51A C51 H51C . . 118(3)
O6 C6 C5 . . 115.8(2)
O6 C6 C7 . . 121.0(2)
C5 C6 C7 . . 123.2(2)
C8 C7 C6 . . 118.2(2)
C8 C7 C71 . . 121.6(2)
C6 C7 C71 . . 120.2(2)
C7 C71 H71A . . 113(3)
C7 C71 H71B . . 111.8(15)
H71A C71 H71B . . 110(2)
C9 C8 C7 . . 117.8(2)
C9 C8 C81 . . 120.4(2)
C7 C8 C81 . . 121.8(2)
C8 C81 H81A . . 106(3)
C8 C81 H81C . . 112(2)
H81A C81 H81C . . 110(3)
C8 C81 H81D . . 117(5)
H81A C81 H81D . . 137(6)
H81C C81 H81D . . 55(2)
C8 C81 H81E . . 114(2)
H81A C81 H81E . . 53(2)
H81C C81 H81E . . 59(3)
H81D C81 H81E . . 106(4)
C8 C9 C10 . . 125.2(2)
C8 C9 O1 . . 113.1(2)
C10 C9 O1 . . 121.8(2)
C9 C10 C5 . . 116.5(2)
C9 C10 C4 . . 117.3(2)
C5 C10 C4 . . 126.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.305(3)
O1 C9 . 1.407(3)
O2 C2 . 1.180(4)
O6 C6 . 1.373(3)
O6 H6 . .92(4)
C2 C3 . 1.530(6)
C2 C3 4_565 1.530(6)
C3 C3 4_565 1.458(12)
C3 C42 4_565 1.510(9)
C3 C4 . 1.558(5)
C3 H3A . 1.01(5)
C3 H3B . 1.11(4)
C4 C42 4_565 1.485(8)
C4 C42 . 1.485(8)
C4 C10 . 1.534(3)
C4 C3 4_565 1.558(5)
C4 C41 . 1.593(8)
C4 C41 4_565 1.593(8)
C41 C42 4_565 1.153(11)
C41 C41 4_565 1.93(2)
C41 H41A . .976(11)
C41 H41B . .959(7)
C41 H41C . .954(6)
C41 H41D . .950(8)
C41 H41E . .966(8)
C41 H41F . .972(9)
C42 C41 4_565 1.153(11)
C42 C3 4_565 1.510(9)
C42 H42A . .968(6)
C42 H42B . .968(7)
C42 H42C . .932(12)
C42 H42D . .944(8)
C42 H42E . .944(8)
C42 H42F . .980(9)
C5 C6 . 1.389(4)
C5 C10 . 1.403(3)
C5 C51 . 1.513(4)
C51 H51A . .96(7)
C51 H51C . .91(3)
C6 C7 . 1.396(4)
C7 C8 . 1.393(3)
C7 C71 . 1.503(3)
C71 H71A . .93(4)
C71 H71B . .95(3)
C8 C9 . 1.384(3)
C8 C81 . 1.499(4)
C81 H81A . 1.02(6)
C81 H81C . 1.05(4)
C81 H81D . 1.00(9)
C81 H81E . .99(4)
C9 C10 . 1.391(3)
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 . . 30.5(2)
C9 O1 C2 C3 . 4_565 -30.5(2)
O2 C2 C3 C3 . 4_565 109.2(3)
O1 C2 C3 C3 . 4_565 -101.54(17)
O2 C2 C3 C42 . 4_565 -162.0(15)
O1 C2 C3 C42 . 4_565 -12.7(17)
C3 C2 C3 C42 4_565 4_565 88.9(16)
O2 C2 C3 C4 . . 150.6(2)
O1 C2 C3 C4 . . -60.1(3)
C3 C2 C3 C4 4_565 . 41.5(3)
C3 C3 C4 C42 4_565 4_565 -156.8(4)
C2 C3 C4 C42 . 4_565 162.0(5)
C3 C3 C4 C42 4_565 . -21.4(4)
C42 C3 C4 C42 4_565 . 135.4(8)
C2 C3 C4 C42 . . -62.6(5)
C3 C3 C4 C10 4_565 . 99.14(16)
C42 C3 C4 C10 4_565 . -104.0(4)
C2 C3 C4 C10 . . 57.9(3)
C42 C3 C4 C3 4_565 4_565 156.8(4)
C2 C3 C4 C3 . 4_565 -41.2(3)
C3 C3 C4 C41 4_565 . -143.9(4)
C42 C3 C4 C41 4_565 . 13.0(6)
C2 C3 C4 C41 . . 174.9(4)
C3 C3 C4 C41 4_565 4_565 -64.1(6)
C42 C3 C4 C41 4_565 4_565 92.7(7)
C2 C3 C4 C41 . 4_565 -105.3(6)
C42 C4 C41 C42 . 4_565 -136.6(7)
C10 C4 C41 C42 . 4_565 97.1(5)
C3 C4 C41 C42 4_565 4_565 -65.6(9)
C3 C4 C41 C42 . 4_565 -16.2(6)
C41 C4 C41 C42 4_565 4_565 -155.2(4)
C42 C4 C41 C41 4_565 4_565 155.2(4)
C42 C4 C41 C41 . 4_565 18.6(3)
C10 C4 C41 C41 . 4_565 -107.6(3)
C3 C4 C41 C41 4_565 4_565 89.7(6)
C3 C4 C41 C41 . 4_565 139.1(3)
C42 C4 C42 C41 4_565 4_565 -73.2(11)
C10 C4 C42 C41 . 4_565 100.6(7)
C3 C4 C42 C41 4_565 4_565 -161.5(7)
C3 C4 C42 C41 . 4_565 -141.0(5)
C41 C4 C42 C41 . 4_565 -26.4(5)
C42 C4 C42 C3 4_565 4_565 88.3(12)
C10 C4 C42 C3 . 4_565 -97.9(3)
C3 C4 C42 C3 . 4_565 20.5(4)
C41 C4 C42 C3 . 4_565 135.1(4)
C41 C4 C42 C3 4_565 4_565 161.5(7)
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 C8 . . 180.0
C2 O1 C9 C10 . . .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 4_565 . -92.2(5)
C42 C4 C10 C9 . . 92.2(5)
C3 C4 C10 C9 4_565 . 29.2(2)
C3 C4 C10 C9 . . -29.2(2)
C41 C4 C10 C9 . . -139.3(3)
C41 C4 C10 C9 4_565 . 139.3(3)
C42 C4 C10 C5 4_565 . 87.8(5)
C42 C4 C10 C5 . . -87.8(5)
C3 C4 C10 C5 4_565 . -150.8(2)
C3 C4 C10 C5 . . 150.8(2)
C41 C4 C10 C5 . . 40.7(3)
C41 C4 C10 C5 4_565 . -40.7(3)
