#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/48/7204878.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_7204878
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         'C10 H8 O2'
_chemical_formula_sum            'C10 H8 O2'
_chemical_formula_weight         160.16
_chemical_name_common            1-(methoxycarbonyl)-4-ethynylbenzene
_chemical_name_systematic
;
1-(methoxycarbonyl)-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   difmap
_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                   13.962(3)
_cell_length_b                   6.052(1)
_cell_length_c                   19.542(3)
_cell_measurement_reflns_used    865
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      12.13
_cell_volume                     1651.3(5)
_computing_cell_refinement       'SMART version 5.049 (Bruker, 1999)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_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      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18903
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_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     141
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0432
_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)+(0.0703P)²+0.3711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                1817
_reflns_number_total             2220
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b404502e.txt
_cod_data_source_block           (2)
_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               7204878
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
O1 O 0.65622(6) 0.11208(13) 0.68178(4) 0.0256(2) Uani 1 1 d . . .
O2 O 0.58544(6) 0.39509(15) 0.73562(4) 0.0301(2) Uani 1 1 d . . .
C1 C 0.61722(7) 0.42581(18) 0.61617(5) 0.0201(2) Uani 1 1 d . . .
C2 C 0.65884(7) 0.33100(19) 0.55829(6) 0.0220(2) Uani 1 1 d . . .
H2 H 0.6883(10) 0.189(3) 0.5615(7) 0.027(3) Uiso 1 1 d . . .
C3 C 0.65699(7) 0.44255(19) 0.49650(6) 0.0233(2) Uani 1 1 d . . .
H3 H 0.6850(10) 0.377(2) 0.4569(8) 0.031(4) Uiso 1 1 d . . .
C4 C 0.61434(7) 0.65123(19) 0.49187(6) 0.0217(2) Uani 1 1 d . . .
C5 C 0.57268(8) 0.74509(19) 0.55011(6) 0.0234(2) Uani 1 1 d . . .
H5 H 0.5429(10) 0.890(2) 0.5472(7) 0.028(3) Uiso 1 1 d . . .
C6 C 0.57384(8) 0.63306(18) 0.61166(6) 0.0228(2) Uani 1 1 d . . .
H6 H 0.5432(11) 0.695(2) 0.6520(8) 0.030(3) Uiso 1 1 d . . .
C7 C 0.61720(7) 0.31371(19) 0.68380(5) 0.0214(2) Uani 1 1 d . . .
C8 C 0.61353(8) 0.77102(19) 0.42832(6) 0.0254(3) Uani 1 1 d . . .
C9 C 0.61174(9) 0.8754(2) 0.37680(6) 0.0304(3) Uani 1 1 d . . .
H9 H 0.6066(12) 0.955(3) 0.3356(9) 0.045(5) Uiso 1 1 d . . .
C10 C 0.65550(9) -0.0071(2) 0.74611(6) 0.0291(3) Uani 1 1 d . . .
H101 H 0.6816(12) -0.152(3) 0.7342(8) 0.041(4) Uiso 1 1 d . . .
H102 H 0.6986(11) 0.071(3) 0.7793(8) 0.038(4) Uiso 1 1 d . . .
H103 H 0.5892(11) -0.017(3) 0.7642(8) 0.036(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
O1 0.0269(4) 0.0234(4) 0.0266(4) 0.0038(3) 0.0028(3) 0.0037(3)
O2 0.0356(5) 0.0322(5) 0.0225(4) -0.0032(3) 0.0007(3) 0.0057(4)
C1 0.0163(5) 0.0216(5) 0.0225(5) -0.0014(4) -0.0012(4) -0.0016(4)
C2 0.0185(5) 0.0205(5) 0.0270(5) -0.0021(4) 0.0017(4) 0.0008(4)
C3 0.0199(5) 0.0261(5) 0.0239(5) -0.0027(4) 0.0020(4) 0.0000(4)
C4 0.0167(5) 0.0247(5) 0.0238(5) 0.0000(4) -0.0018(4) -0.0036(4)
C5 0.0224(5) 0.0204(5) 0.0273(5) -0.0016(4) -0.0027(4) 0.0016(4)
C6 0.0213(5) 0.0232(5) 0.0238(5) -0.0043(4) -0.0008(4) 0.0015(4)
C7 0.0172(5) 0.0229(5) 0.0240(5) -0.0020(4) -0.0019(4) -0.0010(4)
C8 0.0214(5) 0.0273(6) 0.0276(6) -0.0009(5) -0.0009(4) -0.0015(4)
C9 0.0299(6) 0.0341(6) 0.0273(6) 0.0033(5) 0.0011(5) 0.0007(5)
C10 0.0277(6) 0.0292(6) 0.0304(6) 0.0091(5) 0.0015(5) 0.0015(5)
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
C7 O1 C10 115.20(9) . . ?
C2 C1 C6 119.94(10) . . ?
C2 C1 C7 122.25(10) . . ?
C6 C1 C7 117.81(10) . . ?
C3 C2 C1 119.94(10) . . ?
C3 C2 H2 120.4(9) . . ?
C1 C2 H2 119.7(9) . . ?
C2 C3 C4 120.32(10) . . ?
C2 C3 H3 119.9(9) . . ?
C4 C3 H3 119.8(9) . . ?
C5 C4 C3 119.40(10) . . ?
C5 C4 C8 119.65(10) . . ?
C3 C4 C8 120.95(10) . . ?
C6 C5 C4 120.30(10) . . ?
C6 C5 H5 119.9(9) . . ?
C4 C5 H5 119.8(9) . . ?
C5 C6 C1 120.09(10) . . ?
C5 C6 H6 120.9(9) . . ?
C1 C6 H6 119.0(9) . . ?
O2 C7 O1 123.06(10) . . ?
O2 C7 C1 123.96(10) . . ?
O1 C7 C1 112.98(9) . . ?
C9 C8 C4 178.02(13) . . ?
C8 C9 H9 176.6(11) . . ?
O1 C10 H101 103.7(10) . . ?
O1 C10 H102 108.8(9) . . ?
H101 C10 H102 110.7(13) . . ?
O1 C10 H103 110.2(9) . . ?
H101 C10 H103 112.1(13) . . ?
H102 C10 H103 111.0(12) . . ?
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
O1 C7 1.3370(13) . ?
O1 C10 1.4495(14) . ?
O2 C7 1.2102(13) . ?
C1 C2 1.3951(15) . ?
C1 C6 1.3957(15) . ?
C1 C7 1.4856(15) . ?
C2 C3 1.3836(16) . ?
C2 H2 0.955(15) . ?
C3 C4 1.3992(16) . ?
C3 H3 0.953(16) . ?
C4 C5 1.3987(16) . ?
C4 C8 1.4381(16) . ?
C5 C6 1.3808(16) . ?
C5 H5 0.973(14) . ?
C6 H6 0.972(15) . ?
C8 C9 1.1889(17) . ?
C9 H9 0.940(17) . ?
C10 H101 0.980(18) . ?
C10 H102 1.004(16) . ?
C10 H103 0.993(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 O2 0.940(17) 2.175(18) 3.1105(16) 173.2(15) 7_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 555532
