#------------------------------------------------------------------------------
#$Date: 2020-06-20 07:54:35 +0300 (Sat, 20 Jun 2020) $
#$Revision: 253293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243446.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_2243446
loop_
_publ_author_name
'Tiouabi, Mustapha'
'Tabacchi, Raphaël'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of
 6,8-dimethoxy-3-methyl-1H-isochromen-1-one and
 5-bromo-6,8-dimethoxy-3-methyl-1H-isochromen-1-one chloroform
 monosolvate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1107
_journal_page_last               1112
_journal_paper_doi               10.1107/S2056989020007975
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C12 H12 O4'
_chemical_formula_moiety         'C12 H12 O4'
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22
_chemical_name_systematic
;
6,8-Dimethoxy-3-methyl-1H-isochromem-1-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7875(9)
_cell_length_b                   11.3732(12)
_cell_length_c                   14.3637(12)
_cell_measurement_reflns_used    10689
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      1.72
_cell_volume                     2089.0(3)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2005)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2005)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2005)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'φ + ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24778
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.312
_diffrn_reflns_theta_min         2.785
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS; Spek, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+0.3781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                1990
_reflns_number_total             2835
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2010sup1.cif
_cod_data_source_block           I
_cod_database_code               2243446
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.15786(9) 0.27567(12) 0.46504(8) 0.0395(3) Uani d 1 . .
O O2 0.23972(8) 0.33408(10) 0.33972(7) 0.0268(3) Uani d 1 . .
O O3 -0.14208(10) 0.07550(12) 0.14615(9) 0.0404(3) Uani d 1 . .
O O4 -0.01901(9) 0.15403(11) 0.44753(8) 0.0314(3) Uani d 1 . .
C C1 0.01713(12) 0.18950(14) 0.16114(11) 0.0266(3) Uani d 1 . .
H H1 0.024720 0.199167 0.095797 0.032 Uiso calc 1 . .
C C2 -0.06630(12) 0.12755(14) 0.19739(11) 0.0282(3) Uani d 1 . .
C C3 -0.07906(12) 0.11400(14) 0.29319(12) 0.0292(3) Uani d 1 . .
H H3 -0.136951 0.070662 0.316450 0.035 Uiso calc 1 . .
C C4 -0.00875(12) 0.16271(14) 0.35416(11) 0.0258(3) Uani d 1 . .
C C5 0.15644(12) 0.27686(14) 0.38113(11) 0.0263(3) Uani d 1 . .
C C6 0.24844(12) 0.34840(13) 0.24518(10) 0.0248(3) Uani d 1 . .
C C7 0.17841(12) 0.30230(14) 0.18753(10) 0.0248(3) Uani d 1 . .
H H7 0.186695 0.312124 0.122268 0.030 Uiso calc 1 . .
C C8 0.09018(11) 0.23769(13) 0.22263(10) 0.0233(3) Uani d 1 . .
C C9 0.07889(11) 0.22557(13) 0.31981(10) 0.0238(3) Uani d 1 . .
C C10 -0.13653(15) 0.08442(17) 0.04763(13) 0.0387(4) Uani d 1 . .
H H10A -0.068771 0.054680 0.026132 0.058 Uiso calc 1 . .
H H10B -0.144175 0.166918 0.029140 0.058 Uiso calc 1 . .
H H10C -0.192803 0.037821 0.019638 0.058 Uiso calc 1 . .
C C11 -0.10579(14) 0.08855(17) 0.48242(13) 0.0372(4) Uani d 1 . .
H H11A -0.101267 0.007171 0.460350 0.056 Uiso calc 1 . .
H H11B -0.171053 0.123974 0.460230 0.056 Uiso calc 1 . .
H H11C -0.104631 0.089534 0.550635 0.056 Uiso calc 1 . .
C C12 0.34151(12) 0.42031(15) 0.22198(12) 0.0317(4) Uani d 1 . .
H H12A 0.404473 0.381766 0.246095 0.048 Uiso calc 1 . .
H H12B 0.334533 0.498334 0.250262 0.048 Uiso calc 1 . .
H H12C 0.347075 0.428395 0.154231 0.048 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O2 C5 . . 122.97(12) ?
C2 O3 C10 . . 118.34(14) ?
C4 O4 C11 . . 117.52(13) ?
C2 C1 C8 . . 118.58(14) ?
C2 C1 H1 . . 120.7 ?
C8 C1 H1 . . 120.7 ?
O3 C2 C1 . . 124.86(15) ?
O3 C2 C3 . . 113.86(14) ?
C1 C2 C3 . . 121.28(14) ?
C4 C3 C2 . . 120.57(14) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
O4 C4 C3 . . 122.72(14) ?
O4 C4 C9 . . 117.32(14) ?
C3 C4 C9 . . 119.97(14) ?
O1 C5 O2 . . 115.07(14) ?
O1 C5 C9 . . 127.84(15) ?
O2 C5 C9 . . 117.08(13) ?
C7 C6 O2 . . 121.03(14) ?
C7 C6 C12 . . 128.27(15) ?
O2 C6 C12 . . 110.69(13) ?
C6 C7 C8 . . 120.83(14) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C1 C8 C9 . . 121.25(14) ?
C1 C8 C7 . . 120.23(14) ?
C9 C8 C7 . . 118.52(14) ?
C8 C9 C4 . . 118.34(14) ?
C8 C9 C5 . . 119.49(14) ?
C4 C9 C5 . . 122.18(14) ?
O3 C10 H10A . . 109.5 ?
O3 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O3 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C6 C12 H12A . . 109.5 ?
C6 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C6 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.2056(19) ?
O2 C6 . 1.3722(18) ?
O2 C5 . 1.3825(18) ?
O3 C2 . 1.3532(19) ?
O3 C10 . 1.421(2) ?
O4 C4 . 1.3511(19) ?
O4 C11 . 1.427(2) ?
C1 C2 . 1.380(2) ?
C1 C8 . 1.397(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.394(2) ?
C3 C4 . 1.372(2) ?
C3 H3 . 0.9500 ?
C4 C9 . 1.418(2) ?
C5 C9 . 1.449(2) ?
C6 C7 . 1.328(2) ?
C6 C12 . 1.482(2) ?
C7 C8 . 1.438(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.410(2) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 O1 8_565 0.95 2.55 3.366(2) 144 yes
C7 H7 O1 8_565 0.95 2.50 3.3269(19) 146 yes
C12 H12A Cg 6_656 0.98 2.67 3.4902(18) 141 yes
C12 H12B Cg 7_665 0.98 2.88 3.5456(18) 126 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 O3 C2 C1 . . . . 0.0(2) ?
C10 O3 C2 C3 . . . . 179.81(16) ?
C8 C1 C2 O3 . . . . -179.38(16) ?
C8 C1 C2 C3 . . . . 0.8(2) ?
O3 C2 C3 C4 . . . . -179.52(15) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
C11 O4 C4 C3 . . . . 1.6(2) ?
C11 O4 C4 C9 . . . . -178.59(14) ?
C2 C3 C4 O4 . . . . 178.59(15) ?
C2 C3 C4 C9 . . . . -1.2(2) ?
C6 O2 C5 O1 . . . . -177.08(15) ?
C6 O2 C5 C9 . . . . 3.2(2) ?
C5 O2 C6 C7 . . . . -3.2(2) ?
C5 O2 C6 C12 . . . . 175.88(13) ?
O2 C6 C7 C8 . . . . 1.1(2) ?
C12 C6 C7 C8 . . . . -177.82(15) ?
C2 C1 C8 C9 . . . . -1.0(2) ?
C2 C1 C8 C7 . . . . 179.69(15) ?
C6 C7 C8 C1 . . . . -179.92(15) ?
C6 C7 C8 C9 . . . . 0.8(2) ?
C1 C8 C9 C4 . . . . 0.1(2) ?
C7 C8 C9 C4 . . . . 179.43(14) ?
C1 C8 C9 C5 . . . . 179.98(14) ?
C7 C8 C9 C5 . . . . -0.7(2) ?
O4 C4 C9 C8 . . . . -178.83(14) ?
C3 C4 C9 C8 . . . . 1.0(2) ?
O4 C4 C9 C5 . . . . 1.3(2) ?
C3 C4 C9 C5 . . . . -178.86(15) ?
O1 C5 C9 C8 . . . . 179.13(17) ?
O2 C5 C9 C8 . . . . -1.2(2) ?
O1 C5 C9 C4 . . . . -1.0(3) ?
O2 C5 C9 C4 . . . . 178.68(14) ?

_cod_database_fobs_code 2243446
