#------------------------------------------------------------------------------
#$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/18/2011880.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_2011880
loop_
_publ_author_name
'Lawrence, Simon E.'
'Blake, Alexander J.'
'Maguire, Anita R.'
'Moynihan, Edmond J.A.'
_publ_section_title
;
 4-Ethynyl-1,2-methylenedioxybenzene at 150K
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              412
_journal_page_last               413
_journal_paper_doi               10.1107/S0108270100019909
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C9 H6 O2'
_chemical_formula_sum            'C9 H6 O2'
_chemical_formula_weight         146.14
_chemical_melting_point          260
_chemical_name_systematic
;
4-Ethynyl-1,2-methylenedioxybenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 115.03(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.318(3)
_cell_length_b                   15.867(10)
_cell_length_c                   7.571(4)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      12.6
_cell_measurement_theta_min      10.2
_cell_volume                     687.7(7)
_computing_cell_refinement       STADI4
_computing_data_collection       'STADI4 (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL97 and PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       \w/\q
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .196
_diffrn_reflns_av_sigmaI/netI    .117
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5424
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        9.6
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .08
_refine_diff_density_max         .31
_refine_diff_density_min         -.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          .175
_refine_ls_R_factor_gt           .086
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+1.6470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .163
_reflns_number_gt                729
_reflns_number_total             1356
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd1130.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2011880
_cod_database_fobs_code          2011880
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .5011(8) .6364(3) .3161(7) .0200(10) Uani d . 1 . . C
C2 .5051(8) .5596(3) .2221(7) .0217(11) Uani d . 1 . . C
H2 .6127 .5502 .1666 .026 Uiso calc R 1 . . H
C3 .3461(8) .4997(3) .2152(7) .0207(11) Uani d . 1 . . C
C4 .1872(8) .5128(3) .2944(7) .0202(10) Uani d . 1 . . C
C5 .1790(9) .5859(3) .3864(8) .0264(12) Uani d . 1 . . C
H5 .0695 .5941 .4404 .032 Uiso calc R 1 . . H
C6 .3405(8) .6479(3) .3966(7) .0246(12) Uani d . 1 . . C
H6 .3415 .6996 .4602 .029 Uiso calc R 1 . . H
C7 .6634(8) .7028(3) .3289(7) .0218(11) Uani d . 1 . . C
C8 .7933(9) .7584(3) .3412(7) .0287(12) Uani d . 1 . . C
H8 .8977 .8031 .3511 .034 Uiso calc R 1 . . H
O9 .3145(6) .4212(2) .1324(5) .0275(9) Uani d . 1 . . O
C10 .1292(8) .3822(3) .1671(8) .0294(12) Uani d . 1 . . C
H10A .0009 .3648 .0421 .035 Uiso calc R 1 . . H
H10B .1885 .3316 .2499 .035 Uiso calc R 1 . . H
O11 .0461(6) .4430(2) .2634(5) .0296(9) Uani d . 1 . . O
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
C1 .019(2) .021(3) .020(3) .003(2) .008(2) .003(2)
C2 .026(3) .026(3) .017(3) .000(2) .014(2) -.001(2)
C3 .022(2) .019(3) .023(3) .001(2) .012(2) -.003(2)
C4 .021(2) .022(3) .018(3) -.002(2) .008(2) .005(2)
C5 .027(3) .028(3) .032(3) .007(2) .020(2) .004(2)
C6 .027(3) .022(3) .026(3) .007(2) .013(2) .003(2)
C7 .020(2) .022(3) .023(3) .004(2) .009(2) -.001(2)
C8 .027(3) .029(3) .032(3) .000(2) .014(2) -.001(3)
O9 .035(2) .0222(18) .034(2) -.0075(16) .0227(18) -.0065(16)
C10 .031(3) .027(3) .034(3) -.007(2) .017(3) -.004(2)
O11 .0311(19) .032(2) .034(2) -.0039(17) .0217(18) -.0023(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0106 .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
C6 C1 C2 120.1(4)
C6 C1 C7 120.0(4)
C2 C1 C7 119.9(4)
C3 C2 C1 116.6(4)
C2 C3 O9 127.7(4)
C2 C3 C4 122.3(4)
O9 C3 C4 110.0(4)
C5 C4 O11 127.5(4)
C5 C4 C3 122.6(4)
O11 C4 C3 109.9(4)
C4 C5 C6 116.3(4)
C5 C6 C1 122.1(5)
C8 C7 C1 178.3(5)
C3 O9 C10 106.2(3)
O11 C10 O9 107.7(4)
C4 O11 C10 106.1(3)
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 C6 . 1.399(6) ?
C1 C2 . 1.416(6) ?
C1 C7 . 1.444(6) ?
C2 C3 . 1.368(6) ?
C3 O9 . 1.371(5) ?
C3 C4 . 1.385(6) ?
C4 C5 . 1.365(7) ?
C4 O11 . 1.378(6) ?
C5 C6 . 1.396(7) ?
C7 C8 . 1.182(7) ?
O9 C10 . 1.443(5) ?
C10 O11 . 1.435(6) ?
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
C8 H8 O9 2_655 .95 2.58 3.526(7) 178
C2 H2 O9 3_665 .95 2.53 3.344(7) 143
C5 H5 O11 3_566 .95 2.70 3.529(7) 146
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
C6 C1 C2 C3 .2(7)
C7 C1 C2 C3 -179.9(4)
C1 C2 C3 O9 179.6(5)
C1 C2 C3 C4 .4(7)
C2 C3 C4 C5 -.6(7)
O9 C3 C4 C5 -180.0(5)
C2 C3 C4 O11 178.8(5)
O9 C3 C4 O11 -.5(5)
O11 C4 C5 C6 -179.2(5)
C3 C4 C5 C6 .1(7)
C4 C5 C6 C1 .5(7)
C2 C1 C6 C5 -.6(7)
C7 C1 C6 C5 179.4(5)
C2 C3 O9 C10 179.0(5)
C4 C3 O9 C10 -1.7(5)
C3 O9 C10 O11 3.2(5)
C5 C4 O11 C10 -178.1(5)
C3 C4 O11 C10 2.5(5)
O9 C10 O11 C4 -3.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 83663
2 PubChem 92680