#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232833.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_2232833
loop_
_publ_author_name
'Shen, Xu-Ji'
'Zhang, Qun-Zheng'
'Wang, Shi-Xiang'
'Zhang, Ya-Jun'
'Zheng, Xiao-Hui'
_publ_section_title
;
 Isopropyl 3,4-dihydroxybenzoate
;
_journal_coeditor_code           LH5339
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3233
_journal_paper_doi               10.1107/S1600536811044965
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H12 O4'
_chemical_formula_moiety         'C10 H12 O4'
_chemical_formula_sum            'C10 H12 O4'
_chemical_formula_weight         196.20
_chemical_melting_point          407.0(10)
_chemical_name_common            'Isopropyl protocatechuate'
_chemical_name_systematic
;
Isopropyl 3,4-dihydroxybenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.629(3)
_cell_angle_beta                 80.547(3)
_cell_angle_gamma                78.980(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8485(12)
_cell_length_b                   9.1844(17)
_cell_length_c                   9.9834(19)
_cell_measurement_reflns_used    666
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.35
_cell_volume                     499.06(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2520
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.0370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                1289
_reflns_number_total             1745
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5339.cif
_cod_data_source_block           I
_cod_database_code               2232833
_cod_database_fobs_code          2232833
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.2571(2) 0.15042(14) 0.29888(13) 0.0554(4) Uani d . 1 1
O O2 -0.0069(2) 0.13603(15) 0.16625(15) 0.0666(5) Uani d . 1 1
O O3 0.7691(2) -0.42927(15) 0.09653(16) 0.0672(5) Uani d . 1 1
H H3 0.7088 -0.4623 0.0452 0.101 Uiso calc R 1 1
O O4 0.3545(3) -0.32701(15) -0.01531(15) 0.0667(5) Uani d . 1 1
H H4 0.2461 -0.2741 -0.0586 0.100 Uiso calc R 1 1
C C1 -0.0633(5) 0.2409(3) 0.4524(3) 0.0925(9) Uani d . 1 1
H H1A -0.1650 0.1839 0.4288 0.139 Uiso calc R 1 1
H H1B -0.1541 0.3308 0.4754 0.139 Uiso calc R 1 1
H H1C 0.0143 0.1771 0.5321 0.139 Uiso calc R 1 1
C C2 0.2856(5) 0.3780(3) 0.3562(3) 0.0811(7) Uani d . 1 1
H H2A 0.3599 0.3182 0.4385 0.122 Uiso calc R 1 1
H H2B 0.2030 0.4736 0.3715 0.122 Uiso calc R 1 1
H H2C 0.4024 0.3988 0.2762 0.122 Uiso calc R 1 1
C C3 0.1158(4) 0.2893(2) 0.3288(2) 0.0605(6) Uani d . 1 1
H H3A 0.0369 0.3511 0.2462 0.073 Uiso calc R 1 1
C C4 0.1778(3) 0.0861(2) 0.21617(18) 0.0471(5) Uani d . 1 1
C C5 0.3358(3) -0.05140(19) 0.19011(18) 0.0436(4) Uani d . 1 1
C C6 0.2685(3) -0.12546(19) 0.10392(18) 0.0463(5) Uani d . 1 1
H H6 0.1255 -0.0895 0.0673 0.056 Uiso calc R 1 1
C C7 0.4099(3) -0.25143(19) 0.07177(18) 0.0469(5) Uani d . 1 1
C C8 0.6225(3) -0.3068(2) 0.12786(19) 0.0485(5) Uani d . 1 1
C C9 0.6887(3) -0.2345(2) 0.2151(2) 0.0553(5) Uani d . 1 1
H H9 0.8301 -0.2720 0.2534 0.066 Uiso calc R 1 1
C C10 0.5479(3) -0.1072(2) 0.2463(2) 0.0521(5) Uani d . 1 1
H H10 0.5949 -0.0590 0.3047 0.063 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0583(9) 0.0500(8) 0.0628(8) 0.0063(6) -0.0190(7) -0.0256(6)
O2 0.0620(9) 0.0635(9) 0.0807(10) 0.0197(7) -0.0336(8) -0.0342(8)
O3 0.0612(9) 0.0555(8) 0.0889(11) 0.0185(7) -0.0253(8) -0.0338(7)
O4 0.0740(11) 0.0547(8) 0.0803(10) 0.0211(7) -0.0381(8) -0.0354(8)
C1 0.0704(16) 0.107(2) 0.116(2) -0.0091(14) 0.0063(15) -0.0656(18)
C2 0.0992(19) 0.0651(14) 0.0901(17) -0.0163(13) -0.0072(14) -0.0374(13)
C3 0.0705(14) 0.0491(11) 0.0651(13) 0.0111(10) -0.0207(11) -0.0265(10)
C4 0.0507(11) 0.0447(10) 0.0442(10) -0.0008(8) -0.0102(8) -0.0110(8)
C5 0.0439(10) 0.0397(9) 0.0434(10) -0.0011(8) -0.0072(8) -0.0077(8)
C6 0.0433(10) 0.0438(10) 0.0492(10) 0.0045(8) -0.0136(8) -0.0115(8)
C7 0.0518(11) 0.0398(10) 0.0491(10) 0.0002(8) -0.0119(8) -0.0133(8)
C8 0.0461(11) 0.0407(10) 0.0540(11) 0.0027(8) -0.0091(8) -0.0101(8)
C9 0.0452(11) 0.0516(11) 0.0684(13) 0.0057(9) -0.0203(9) -0.0166(9)
C10 0.0521(11) 0.0488(11) 0.0580(11) -0.0020(9) -0.0159(9) -0.0172(9)
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
C4 O1 C3 118.03(14)
C8 O3 H3 109.5
C7 O4 H4 109.5
C3 C1 H1A 109.5
C3 C1 H1B 109.5
H1A C1 H1B 109.5
C3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 H2A 109.5
C3 C2 H2B 109.5
H2A C2 H2B 109.5
C3 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
O1 C3 C1 108.46(17)
O1 C3 C2 105.88(17)
C1 C3 C2 113.43(18)
O1 C3 H3A 109.7
C1 C3 H3A 109.7
C2 C3 H3A 109.7
O2 C4 O1 123.08(16)
O2 C4 C5 123.18(17)
O1 C4 C5 113.73(15)
C6 C5 C10 119.21(16)
C6 C5 C4 117.83(16)
C10 C5 C4 122.95(17)
C7 C6 C5 121.01(16)
C7 C6 H6 119.5
C5 C6 H6 119.5
O4 C7 C6 123.48(16)
O4 C7 C8 116.86(15)
C6 C7 C8 119.66(16)
O3 C8 C9 119.09(16)
O3 C8 C7 121.41(16)
C9 C8 C7 119.49(16)
C8 C9 C10 120.90(17)
C8 C9 H9 119.6
C10 C9 H9 119.6
C9 C10 C5 119.73(18)
C9 C10 H10 120.1
C5 C10 H10 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.330(2)
O1 C3 1.464(2)
O2 C4 1.215(2)
O3 C8 1.361(2)
O3 H3 0.8200
O4 C7 1.372(2)
O4 H4 0.8200
C1 C3 1.497(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.502(3)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 H3A 0.9800
C4 C5 1.479(2)
C5 C6 1.386(2)
C5 C10 1.389(3)
C6 C7 1.377(2)
C6 H6 0.9300
C7 C8 1.391(3)
C8 C9 1.380(3)
C9 C10 1.381(3)
C9 H9 0.9300
C10 H10 0.9300
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
O3 H3 O4 2_645 0.820 2.150 2.844(2) 142.27 yes
O3 H3 O4 1_555 0.820 2.276 2.720(2) 114.47 yes
O4 H4 O2 2_555 0.820 1.929 2.747(2) 175.23 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
C4 O1 C3 C1 85.7(2)
C4 O1 C3 C2 -152.21(17)
C3 O1 C4 O2 -0.9(3)
C3 O1 C4 C5 178.76(15)
O2 C4 C5 C6 0.3(3)
O1 C4 C5 C6 -179.44(15)
O2 C4 C5 C10 179.34(18)
O1 C4 C5 C10 -0.4(3)
C10 C5 C6 C7 -1.0(3)
C4 C5 C6 C7 178.12(15)
C5 C6 C7 O4 -178.53(17)
C5 C6 C7 C8 0.8(3)
O4 C7 C8 O3 0.6(3)
C6 C7 C8 O3 -178.80(16)
O4 C7 C8 C9 179.39(17)
C6 C7 C8 C9 0.0(3)
O3 C8 C9 C10 178.19(17)
C7 C8 C9 C10 -0.6(3)
C8 C9 C10 C5 0.5(3)
C6 C5 C10 C9 0.3(3)
C4 C5 C10 C9 -178.72(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9496468
