#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/14/2221496.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_2221496
loop_
_publ_author_name
'Wei, Mei-yan'
'Liu, Zhen'
'Zhang, Xiu-li'
'Shao, Chang-lun'
'Wang, Chang-yun'
_publ_section_title
;
 Methyl 3-hydroxy-4-(3-methylbut-2-enyloxy)benzoate
;
_journal_coeditor_code           SJ2576
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o734
_journal_page_last               o735
_journal_paper_doi               10.1107/S160053680900806X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H16 O4'
_chemical_formula_moiety         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_chemical_name_systematic
;
Methyl 3-hydroxy-4-(3-methylbut-2-enyloxy)benzoate
;
_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                100.655(3)
_cell_angle_beta                 98.771(3)
_cell_angle_gamma                115.456(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8401(16)
_cell_length_b                   8.3899(17)
_cell_length_c                   11.099(2)
_cell_measurement_reflns_used    4817
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.93
_cell_volume                     625.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4817
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1024P)²+0.0667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1609
_reflns_number_gt                2058
_reflns_number_total             2420
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2576.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221496
_cod_database_fobs_code          2221496
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_disorder_assembly
_atom_site_disorder_group
C C1 -0.4408(3) 0.2951(3) 0.50642(16) 0.0716(5) Uani d . 1 . .
H H1A -0.3697 0.3458 0.5944 0.107 Uiso calc R 1 . .
H H1B -0.4681 0.1692 0.4784 0.107 Uiso calc R 1 . .
H H1C -0.5616 0.3009 0.4960 0.107 Uiso calc R 1 . .
C C2 -0.4029(2) 0.34671(19) 0.30738(14) 0.0490(4) Uani d . 1 . .
C C3 -0.2748(2) 0.46837(17) 0.24198(13) 0.0453(3) Uani d . 1 . .
C C4 -0.0924(2) 0.61796(19) 0.30835(13) 0.0481(4) Uani d . 1 . .
H H4A -0.0474 0.6410 0.3955 0.058 Uiso calc R 1 . .
C C5 0.02077(19) 0.73115(19) 0.24510(13) 0.0457(3) Uani d . 1 . .
C C6 -0.04479(19) 0.69490(18) 0.11391(13) 0.0452(3) Uani d . 1 . .
C C7 -0.2253(2) 0.5465(2) 0.04830(14) 0.0558(4) Uani d . 1 . .
H H7A -0.2702 0.5224 -0.0389 0.067 Uiso calc R 1 . .
C C8 -0.3388(2) 0.4343(2) 0.11268(14) 0.0544(4) Uani d . 1 . .
H H8A -0.4597 0.3346 0.0682 0.065 Uiso calc R 1 . .
C C9 0.0269(2) 0.7902(2) -0.07071(14) 0.0557(4) Uani d . 1 . .
H H9A -0.0895 0.8036 -0.0942 0.067 Uiso calc R 1 . .
H H9B 0.0003 0.6684 -0.1169 0.067 Uiso calc R 1 . .
C C10 0.1952(2) 0.9336(2) -0.10072(15) 0.0578(4) Uani d . 1 . .
H H10A 0.3061 1.0114 -0.0342 0.069 Uiso calc R 1 . .
C C11 0.1993(2) 0.9589(2) -0.21421(14) 0.0546(4) Uani d . 1 . .
C C12 0.0315(3) 0.8410(3) -0.32730(17) 0.0836(6) Uani d . 1 . .
H H12A -0.0725 0.7516 -0.3026 0.125 Uiso calc R 1 . .
H H12B 0.0724 0.7793 -0.3892 0.125 Uiso calc R 1 . .
H H12C -0.0138 0.9160 -0.3632 0.125 Uiso calc R 1 . .
C C13 0.3751(3) 1.1067(3) -0.2368(2) 0.0752(5) Uani d . 1 . .
H H13A 0.4748 1.1741 -0.1582 0.113 Uiso calc R 1 . .
H H13B 0.3387 1.1889 -0.2699 0.113 Uiso calc R 1 . .
H H13C 0.4242 1.0518 -0.2968 0.113 Uiso calc R 1 . .
O O1 -0.32509(16) 0.39913(15) 0.43211(10) 0.0640(4) Uani d . 1 . .
O O2 -0.56125(16) 0.21602(16) 0.25485(12) 0.0702(4) Uani d . 1 . .
O O3 0.19557(16) 0.87793(16) 0.31218(11) 0.0663(4) Uani d . 1 . .
H H3A 0.231(4) 0.943(4) 0.263(2) 0.102(8) Uiso d . 1 . .
O O4 0.08089(14) 0.81567(13) 0.06303(9) 0.0537(3) Uani d . 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
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 O1 . . 123.26(13) ?
O2 C2 C3 . . 124.42(14) ?
O1 C2 C3 . . 112.31(12) ?
C8 C3 C4 . . 119.39(13) ?
C8 C3 C2 . . 118.91(13) ?
C4 C3 C2 . . 121.69(13) ?
C5 C4 C3 . . 120.19(13) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
O3 C5 C4 . . 119.06(13) ?
O3 C5 C6 . . 120.93(12) ?
C4 C5 C6 . . 120.01(12) ?
O4 C6 C7 . . 126.11(13) ?
O4 C6 C5 . . 114.18(12) ?
C7 C6 C5 . . 119.71(13) ?
C8 C7 C6 . . 119.92(14) ?
C8 C7 H7A . . 120.0 ?
C6 C7 H7A . . 120.0 ?
C3 C8 C7 . . 120.78(13) ?
C3 C8 H8A . . 119.6 ?
C7 C8 H8A . . 119.6 ?
O4 C9 C10 . . 106.75(12) ?
O4 C9 H9A . . 110.4 ?
C10 C9 H9A . . 110.4 ?
O4 C9 H9B . . 110.4 ?
C10 C9 H9B . . 110.4 ?
H9A C9 H9B . . 108.6 ?
C11 C10 C9 . . 125.11(15) ?
C11 C10 H10A . . 117.4 ?
C9 C10 H10A . . 117.4 ?
C10 C11 C12 . . 121.92(15) ?
C10 C11 C13 . . 121.91(16) ?
C12 C11 C13 . . 116.16(15) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C2 O1 C1 . . 117.18(12) ?
C5 O3 H3A . . 105.7(18) ?
C6 O4 C9 . . 118.40(11) ?
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
C1 O1 . 1.4418(17) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O2 . 1.2066(18) ?
C2 O1 . 1.3300(18) ?
C2 C3 . 1.4808(18) ?
C3 C8 . 1.378(2) ?
C3 C4 . 1.399(2) ?
C4 C5 . 1.3763(18) ?
C4 H4A . 0.9300 ?
C5 O3 . 1.3594(17) ?
C5 C6 . 1.397(2) ?
C6 O4 . 1.3563(16) ?
C6 C7 . 1.386(2) ?
C7 C8 . 1.382(2) ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 O4 . 1.4289(18) ?
C9 C10 . 1.489(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.319(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.484(3) ?
C11 C13 . 1.500(2) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
O3 H3A . 0.84(3) ?
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
O3 H3A O4 . 0.84(3) 2.16(2) 2.6519(15) 117(2)
O3 H3A O2 1_665 0.84(3) 2.20(3) 2.9111(16) 143(2)
C9 H9B Cg1 2_565 0.97 2.90 3.7483(2) 146
C13 H13B Cg1 2_575 0.96 2.96 3.688(3) 134
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
O2 C2 C3 C8 . . . . 0.9(2) ?
O1 C2 C3 C8 . . . . -178.13(12) ?
O2 C2 C3 C4 . . . . -179.95(14) ?
O1 C2 C3 C4 . . . . 1.0(2) ?
C8 C3 C4 C5 . . . . 0.8(2) ?
C2 C3 C4 C5 . . . . -178.28(12) ?
C3 C4 C5 O3 . . . . 178.57(13) ?
C3 C4 C5 C6 . . . . -1.2(2) ?
O3 C5 C6 O4 . . . . 0.8(2) ?
C4 C5 C6 O4 . . . . -179.48(12) ?
O3 C5 C6 C7 . . . . -178.70(14) ?
C4 C5 C6 C7 . . . . 1.0(2) ?
O4 C6 C7 C8 . . . . -179.96(13) ?
C5 C6 C7 C8 . . . . -0.6(2) ?
C4 C3 C8 C7 . . . . -0.3(2) ?
C2 C3 C8 C7 . . . . 178.79(13) ?
C6 C7 C8 C3 . . . . 0.2(3) ?
O4 C9 C10 C11 . . . . -177.76(15) ?
C9 C10 C11 C12 . . . . -0.9(3) ?
C9 C10 C11 C13 . . . . -179.89(15) ?
O2 C2 O1 C1 . . . . -1.6(2) ?
C3 C2 O1 C1 . . . . 177.47(13) ?
C7 C6 O4 C9 . . . . -0.6(2) ?
C5 C6 O4 C9 . . . . 179.99(12) ?
C10 C9 O4 C6 . . . . -176.59(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741906
