#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/57/2005742.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_2005742
loop_
_publ_author_name
'Clegg, W.'
'Al Dulayymi, A. R.'
'Baird, M. S.'
_publ_section_title
;
 A Strained Cyclononadienyne
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              3219
_journal_page_last               3222
_journal_paper_doi               10.1107/S0108270196012152
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C12 H11 Cl O2'
_chemical_formula_weight         222.66
_chemical_name_systematic
;
 methyl 8-chlorobicyclo[7.1.0]deca-1,8-dien-4-yn-2-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.743(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8887(10)
_cell_length_b                   20.4239(13)
_cell_length_c                   7.1847(5)
_cell_measurement_reflns_used    6551
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.78
_cell_volume                     2146.5(2)
_computing_cell_refinement       'local programs'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13439
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       0.0010(4)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_all   1.020
_refine_ls_goodness_of_fit_obs   1.109
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_restrained_S_obs      1.109
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_obs          0.0454
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.048P)²+0.58P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1133
_refine_ls_wR_factor_obs         0.0999
_reflns_number_observed          3362
_reflns_number_total             4994
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            bm1113.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.048P)^2^+0.58P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.048P)^2^+0.58P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C1 1 0.41091(13) 0.72031(9) 0.2310(3) 0.0231(4) Uani d . C
C2 1 0.31691(14) 0.69465(9) 0.2244(3) 0.0282(5) Uani d . C
H2A 1 0.2729 0.6978 0.1032 0.034 Uiso calc R H
H2B 1 0.2899 0.6987 0.3398 0.034 Uiso calc R H
C3 1 0.39813(13) 0.65093(9) 0.2323(3) 0.0235(4) Uani d . C
C4 1 0.42456(14) 0.58904(9) 0.2594(3) 0.0252(4) Uani d . C
C5 1 0.51750(14) 0.55750(10) 0.3038(3) 0.0302(5) Uani d . C
H5A 1 0.5095 0.5094 0.2949 0.036 Uiso calc R H
H5B 1 0.5454 0.5679 0.4366 0.036 Uiso calc R H
C6 1 0.58421(15) 0.57786(11) 0.1765(3) 0.0339(5) Uani d . C
H6A 1 0.6436 0.5556 0.2184 0.041 Uiso calc R H
H6B 1 0.5599 0.5645 0.0443 0.041 Uiso calc R H
C7 1 0.59723(14) 0.64884(11) 0.1856(3) 0.0310(5) Uani d . C
C8 1 0.59215(14) 0.70665(11) 0.1991(3) 0.0297(5) Uani d . C
C9 1 0.56111(14) 0.77416(10) 0.2103(3) 0.0292(5) Uani d . C
H9A 1 0.5692 0.7986 0.0955 0.035 Uiso calc R H
H9B 1 0.5977 0.7961 0.3221 0.035 Uiso calc R H
C10 1 0.46133(14) 0.77389(9) 0.2264(3) 0.0244(4) Uani d . C
C11 1 0.42039(15) 0.84037(10) 0.2342(3) 0.0281(5) Uani d . C
C12 1 0.28951(17) 0.90193(10) 0.2562(3) 0.0400(6) Uani d . C
H12A 1 0.3202 0.9251 0.3698 0.060 Uiso calc R H
H12B 1 0.2248 0.8960 0.2621 0.060 Uiso calc R H
H12C 1 0.2948 0.9275 0.1434 0.060 Uiso calc R H
O1 1 0.46356(11) 0.89009(7) 0.2308(2) 0.0384(4) Uani d . O
O2 1 0.33185(10) 0.83865(7) 0.2463(2) 0.0336(4) Uani d . O
Cl1 1 0.33526(4) 0.53249(2) 0.26229(8) 0.03676(16) Uani d . Cl
C13 1 0.91919(13) 0.71978(9) 0.2029(3) 0.0229(4) Uani d . C
C14 1 0.82487(14) 0.69550(10) 0.1330(3) 0.0300(5) Uani d . C
H14A 1 0.7990 0.7003 -0.0035 0.036 Uiso calc R H
H14B 1 0.7801 0.6989 0.2187 0.036 Uiso calc R H
C15 1 0.90493(13) 0.65084(9) 0.1890(3) 0.0233(4) Uani d . C
C16 1 0.92982(14) 0.58863(10) 0.1846(3) 0.0264(4) Uani d . C
C17 1 1.02217(16) 0.55677(10) 0.2110(3) 0.0362(5) Uani d . C
H17A 1 1.0496 0.5671 0.0991 0.043 Uiso calc R H
H17B 1 1.0134 0.5087 0.2128 0.043 Uiso calc R H
C18 1 1.08988(16) 0.57578(11) 0.3867(3) 0.0389(6) Uani d . C
H18A 1 1.0667 0.5616 0.5009 0.047 Uiso calc R H
H18B 1 1.1489 0.5535 0.3868 0.047 Uiso calc R H
C19 1 1.10377(15) 0.64712(11) 0.3923(3) 0.0328(5) Uani d . C
C20 1 1.09956(14) 0.70510(11) 0.3790(3) 0.0279(5) Uani d . C
C21 1 1.06957(14) 0.77291(10) 0.3435(3) 0.0279(5) Uani d . C
H21A 1 1.1067 0.7945 0.2603 0.033 Uiso calc R H
H21B 1 1.0778 0.7973 0.4646 0.033 Uiso calc R H
C22 1 0.96978(14) 0.77325(9) 0.2495(3) 0.0235(4) Uani d . C
C23 1 0.92903(16) 0.83945(10) 0.2114(3) 0.0284(5) Uani d . C
C24 1 0.7954(2) 0.90050(11) 0.0995(4) 0.0484(7) Uani d . C
H24A 1 0.8054 0.9268 0.2157 0.073 Uiso calc R H
H24B 1 0.7296 0.8940 0.0555 0.073 Uiso calc R H
H24C 1 0.8211 0.9233 0.0015 0.073 Uiso calc R H
O3 1 0.97250(12) 0.88944(7) 0.2437(2) 0.0396(4) Uani d . O
O4 1 0.83958(11) 0.83762(7) 0.1376(2) 0.0369(4) Uani d . O
Cl2 1 0.83931(4) 0.53314(3) 0.11172(8) 0.03696(16) Uani d . Cl
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C10 C1 C3 153.03(19) yes
C10 C1 C2 145.18(19) ?
C3 C1 C2 61.66(13) yes
C1 C2 C3 57.29(13) yes
C4 C3 C1 155.3(2) yes
C4 C3 C2 142.13(19) ?
C1 C3 C2 61.04(13) yes
C3 C4 C5 132.38(18) yes
C3 C4 Cl1 114.95(16) ?
C5 C4 Cl1 112.48(14) ?
C4 C5 C6 115.54(17) yes
C7 C6 C5 109.80(17) yes
C8 C7 C6 168.2(2) yes
C7 C8 C9 165.4(2) yes
C8 C9 C10 109.04(17) yes
C1 C10 C11 120.70(19) ?
C1 C10 C9 124.89(18) yes
C11 C10 C9 114.41(17) ?
O1 C11 O2 124.03(19) ?
O1 C11 C10 122.9(2) ?
O2 C11 C10 113.12(17) ?
C11 O2 C12 115.08(17) ?
C22 C13 C15 153.7(2) yes
C22 C13 C14 144.32(19) ?
C15 C13 C14 61.79(13) yes
C13 C14 C15 57.10(13) yes
C16 C15 C13 155.5(2) yes
C16 C15 C14 142.25(19) ?
C13 C15 C14 61.11(13) yes
C15 C16 C17 131.77(19) yes
C15 C16 Cl2 114.93(16) ?
C17 C16 Cl2 112.95(14) ?
C16 C17 C18 116.51(18) yes
C19 C18 C17 110.20(19) yes
C20 C19 C18 168.4(2) yes
C19 C20 C21 165.2(2) yes
C20 C21 C22 108.94(16) yes
C13 C22 C23 120.44(19) ?
C13 C22 C21 124.75(18) yes
C23 C22 C21 114.81(17) ?
O3 C23 O4 123.9(2) ?
O3 C23 C22 123.2(2) ?
O4 C23 C22 112.91(18) ?
C23 O4 C24 115.73(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C10 1.331(3) yes
C1 C3 1.430(3) yes
C1 C2 1.487(3) yes
C2 C3 1.496(3) yes
C3 C4 1.327(3) yes
C4 C5 1.506(3) yes
C4 Cl1 1.764(2) ?
C5 C6 1.528(3) yes
C6 C7 1.463(3) yes
C7 C8 1.188(3) yes
C8 C9 1.461(3) yes
C9 C10 1.512(3) yes
C10 C11 1.494(3) ?
C11 O1 1.205(2) ?
C11 O2 1.338(3) ?
C12 O2 1.446(2) ?
C13 C22 1.333(3) yes
C13 C15 1.425(3) yes
C13 C14 1.486(3) yes
C14 C15 1.495(3) yes
C15 C16 1.326(3) yes
C16 C17 1.501(3) yes
C16 Cl2 1.764(2) ?
C17 C18 1.512(3) yes
C18 C19 1.471(3) yes
C19 C20 1.189(3) yes
C20 C21 1.463(3) yes
C21 C22 1.513(3) yes
C22 C23 1.486(3) ?
C23 O3 1.208(2) ?
C23 O4 1.339(3) ?
C24 O4 1.446(2) ?
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_publ_flag
C10 C1 C2 C3 176.4(4) ?
C3 C1 C2 C3 0.0 ?
C10 C1 C3 C4 21.6(8) yes
C2 C1 C3 C4 -162.9(5) ?
C10 C1 C3 C2 -175.4(5) ?
C2 C1 C3 C2 0.0 ?
C1 C2 C3 C4 168.5(3) ?
C1 C2 C3 C1 0.0 ?
C1 C3 C4 C5 -8.8(6) yes
C2 C3 C4 C5 -164.0(3) ?
C1 C3 C4 Cl1 165.7(4) ?
C2 C3 C4 Cl1 10.4(4) ?
C3 C4 C5 C6 -49.9(3) yes
Cl1 C4 C5 C6 135.61(16) ?
C4 C5 C6 C7 57.8(2) yes
C5 C6 C7 C8 -29.4(12) ?
C6 C7 C8 C9 -15.1(19) ?
C7 C8 C9 C10 9.8(10) ?
C3 C1 C10 C11 -178.6(3) ?
C2 C1 C10 C11 8.4(4) ?
C3 C1 C10 C9 2.4(5) ?
C2 C1 C10 C9 -170.6(3) ?
C8 C9 C10 C1 0.5(3) ?
C8 C9 C10 C11 -178.57(17) ?
C1 C10 C11 O1 179.8(2) ?
C9 C10 C11 O1 -1.1(3) ?
C1 C10 C11 O2 0.2(3) ?
C9 C10 C11 O2 179.27(17) ?
O1 C11 O2 C12 -0.3(3) ?
C10 C11 O2 C12 179.38(17) ?
C22 C13 C14 C15 -176.3(3) ?
C15 C13 C14 C15 0.0 ?
C22 C13 C15 C16 -19.4(8) yes
C14 C13 C15 C16 165.5(5) ?
C22 C13 C15 C14 175.1(4) ?
C14 C13 C15 C14 0.0 ?
C13 C14 C15 C16 -170.2(3) ?
C13 C14 C15 C13 0.0 ?
C13 C15 C16 C17 4.2(6) yes
C14 C15 C16 C17 163.2(3) ?
C13 C15 C16 Cl2 -168.4(4) ?
C14 C15 C16 Cl2 -9.4(4) ?
C15 C16 C17 C18 51.3(3) yes
Cl2 C16 C17 C18 -135.95(18) ?
C16 C17 C18 C19 -56.9(3) yes
C17 C18 C19 C20 28.5(12) ?
C18 C19 C20 C21 9.3(18) ?
C19 C20 C21 C22 -4.2(9) ?
C15 C13 C22 C23 179.4(3) ?
C14 C13 C22 C23 -8.1(4) ?
C15 C13 C22 C21 -1.1(5) ?
C14 C13 C22 C21 171.5(3) ?
C20 C21 C22 C13 -1.7(3) ?
C20 C21 C22 C23 177.86(16) ?
C13 C22 C23 O3 -176.91(19) ?
C21 C22 C23 O3 3.5(3) ?
C13 C22 C23 O4 2.9(3) ?
C21 C22 C23 O4 -176.65(16) ?
O3 C23 O4 C24 -1.0(3) ?
C22 C23 O4 C24 179.19(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24728716
