#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/48/7204877.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204877
loop_
_publ_author_name
'Dai, Chaoyang'
'Yuan, Zheng'
'Collings, Jonathan C.'
'Fasina, Tolulope M.'
'Thomas, Rhodri Ll.'
'Roscoe, Karl P.'
'Stimson, Lorna M.'
'Yufit, Dmitry S.'
'Batsanov, Andrei S.'
'Howard, Judith A. K.'
'Marder, Todd B.'
_publ_section_title
;
 Crystal engineering with p-substituted 4-ethynylbenzenes using the
 C?H?O supramolecular synthon
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              184
_journal_paper_doi               10.1039/b404502e
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C9 H8 O'
_chemical_formula_sum            'C9 H8 O'
_chemical_formula_weight         132.15
_chemical_name_common            1-methoxy-4-ethynylbenzene
_chemical_name_systematic        ' 1-methoxy-4-ethynylbenzene'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.027(5)
_cell_length_b                   6.124(2)
_cell_length_c                   17.047(6)
_cell_measurement_reflns_used    665
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.20
_cell_measurement_theta_min      17.18
_cell_volume                     1464.4(9)
_computing_cell_refinement       'SMART version 5.054 (Bruker, 1998)'
_computing_data_collection       'SMART version 5.054 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.01 (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material  'SHELXTL version 5.10 (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       '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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10272
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0372
_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)+(0.0510P)²+0.4494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                1705
_reflns_number_total             1923
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b404502e.txt
_cod_data_source_block           (1)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7204877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.39314(5) 0.67850(11) 0.28286(4) 0.02496(18) Uani 1 1 d . . .
C1 C 0.38907(6) 0.58329(15) 0.35602(5) 0.0202(2) Uani 1 1 d . . .
C2 C 0.34071(7) 0.67188(16) 0.42016(5) 0.0225(2) Uani 1 1 d . . .
H2 H 0.3074(9) 0.812(2) 0.4157(7) 0.028(3) Uiso 1 1 d . . .
C3 C 0.34065(6) 0.55886(16) 0.49149(6) 0.0230(2) Uani 1 1 d . . .
H3 H 0.3072(9) 0.619(2) 0.5369(7) 0.029(3) Uiso 1 1 d . . .
C4 C 0.38730(6) 0.35813(15) 0.49921(5) 0.0210(2) Uani 1 1 d . . .
C5 C 0.43620(6) 0.27253(15) 0.43387(6) 0.0223(2) Uani 1 1 d . . .
H5 H 0.4682(9) 0.134(2) 0.4383(7) 0.026(3) Uiso 1 1 d . . .
C6 C 0.43733(6) 0.38431(15) 0.36312(5) 0.0222(2) Uani 1 1 d . . .
H6 H 0.4714(10) 0.327(2) 0.3169(8) 0.035(3) Uiso 1 1 d . . .
C7 C 0.33647(8) 0.87009(17) 0.26986(6) 0.0296(2) Uani 1 1 d . . .
H71 H 0.3465(10) 0.912(3) 0.2138(9) 0.041(4) Uiso 1 1 d . . .
H72 H 0.2666(11) 0.836(2) 0.2798(7) 0.038(4) Uiso 1 1 d . . .
H73 H 0.3571(11) 0.994(3) 0.3038(9) 0.042(4) Uiso 1 1 d . . .
C8 C 0.38541(6) 0.23946(17) 0.57219(6) 0.0239(2) Uani 1 1 d . . .
C9 C 0.38368(7) 0.13613(18) 0.63188(6) 0.0285(2) Uani 1 1 d . . .
H9 H 0.3848(10) 0.053(2) 0.6796(9) 0.040(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0297(4) 0.0256(3) 0.0195(3) 0.0012(3) 0.0019(3) 0.0025(3)
C1 0.0196(4) 0.0221(4) 0.0191(4) -0.0009(3) -0.0008(3) -0.0035(3)
C2 0.0229(4) 0.0213(4) 0.0232(4) -0.0021(3) 0.0011(3) 0.0013(3)
C3 0.0219(4) 0.0259(5) 0.0211(4) -0.0031(3) 0.0024(3) 0.0003(3)
C4 0.0182(4) 0.0240(4) 0.0207(4) -0.0008(3) -0.0013(3) -0.0028(3)
C5 0.0214(4) 0.0213(4) 0.0243(4) -0.0015(3) -0.0008(3) 0.0016(3)
C6 0.0214(4) 0.0241(4) 0.0211(4) -0.0036(3) 0.0017(3) 0.0009(3)
C7 0.0371(6) 0.0249(5) 0.0267(5) 0.0031(4) -0.0001(4) 0.0035(4)
C8 0.0215(4) 0.0260(4) 0.0243(4) -0.0015(3) -0.0005(3) -0.0009(4)
C9 0.0297(5) 0.0312(5) 0.0245(5) 0.0017(4) 0.0007(4) 0.0003(4)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O C7 117.59(7) . . ?
O C1 C2 124.36(9) . . ?
O C1 C6 115.26(8) . . ?
C2 C1 C6 120.38(9) . . ?
C1 C2 C3 119.25(9) . . ?
C1 C2 H2 120.8(7) . . ?
C3 C2 H2 120.0(7) . . ?
C4 C3 C2 121.08(8) . . ?
C4 C3 H3 118.8(7) . . ?
C2 C3 H3 120.1(7) . . ?
C3 C4 C5 118.70(8) . . ?
C3 C4 C8 121.05(8) . . ?
C5 C4 C8 120.25(9) . . ?
C6 C5 C4 120.62(9) . . ?
C6 C5 H5 119.8(7) . . ?
C4 C5 H5 119.6(7) . . ?
C5 C6 C1 119.96(8) . . ?
C5 C6 H6 121.6(8) . . ?
C1 C6 H6 118.4(8) . . ?
O C7 H71 106.4(9) . . ?
O C7 H72 109.9(8) . . ?
H71 C7 H72 110.4(11) . . ?
O C7 H73 111.8(9) . . ?
H71 C7 H73 108.5(12) . . ?
H72 C7 H73 109.8(11) . . ?
C9 C8 C4 178.41(11) . . ?
C8 C9 H9 177.9(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.3778(11) . ?
O C7 1.4345(13) . ?
C1 C2 1.3964(13) . ?
C1 C6 1.3992(13) . ?
C2 C3 1.3991(14) . ?
C2 H2 0.981(13) . ?
C3 C4 1.3988(14) . ?
C3 H3 0.978(13) . ?
C4 C5 1.4092(13) . ?
C4 C8 1.4410(13) . ?
C5 C6 1.3869(13) . ?
C5 H5 0.960(13) . ?
C6 H6 0.986(14) . ?
C7 H71 0.999(15) . ?
C7 H72 1.016(15) . ?
C7 H73 0.996(16) . ?
C8 C9 1.1985(15) . ?
C9 H9 0.960(15) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O 0.960(15) 2.263(15) 3.2179(15) 173.0(12) 7_566
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 O C7 -6.25(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 219872
