#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503866.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_1503866
loop_
_publ_author_name
'Deng, Youqian'
'Jin, Xin'
'Fu, Chunling'
'Ma, Shengming'
_publ_section_title
;
 Efficient highly selective synthesis of methyl
 2-(ethynyl)alk-2(E)-enoates and 2-(1'-chlorovinyl)alk-2(Z)-enoates from
 2-(methoxycarbonyl)-2,3-allenols.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2169
_journal_page_last               2172
_journal_paper_doi               10.1021/ol9004273
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C14 H13 Cl O2'
_chemical_formula_weight         248.69
_chemical_name_systematic
; 
 ? 
;
_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'
_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                 99.353(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9734(5)
_cell_length_b                   16.9107(10)
_cell_length_c                   9.8279(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1307.54(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14705
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.797844
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.452
_exptl_crystal_size_min          0.266
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0425
_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)+(0.0574P)²+0.4110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                2005
_reflns_number_total             2303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9004273_si_003.cif
_cod_data_source_block           z
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503866
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_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
Cl1 Cl 0.21223(10) 0.37063(4) 0.79342(6) 0.0916(3) Uani 1 1 d .
O1 O 0.3564(2) 0.60011(9) 0.61999(17) 0.0847(5) Uani 1 1 d .
O2 O 0.46510(19) 0.51663(8) 0.78580(14) 0.0721(4) Uani 1 1 d .
C1 C -0.1409(3) 0.41387(13) 0.0232(2) 0.0714(6) Uani 1 1 d .
H1A H -0.1453 0.4685 0.0127 0.086 Uiso 1 1 calc R
C2 C -0.2269(3) 0.36652(15) -0.0793(2) 0.0802(6) Uani 1 1 d .
H2A H -0.2882 0.3894 -0.1581 0.096 Uiso 1 1 calc R
C3 C -0.2223(3) 0.28624(15) -0.0653(2) 0.0807(6) Uani 1 1 d .
H3A H -0.2803 0.2543 -0.1343 0.097 Uiso 1 1 calc R
C4 C -0.1317(3) 0.25302(15) 0.0511(3) 0.0872(7) Uani 1 1 d .
H4A H -0.1291 0.1983 0.0609 0.105 Uiso 1 1 calc R
C5 C -0.0449(3) 0.29958(13) 0.1534(2) 0.0752(6) Uani 1 1 d .
H5A H 0.0166 0.2760 0.2314 0.090 Uiso 1 1 calc R
C6 C -0.0477(2) 0.38133(11) 0.14191(19) 0.0582(5) Uani 1 1 d .
C7 C 0.0407(2) 0.43349(12) 0.2472(2) 0.0614(5) Uani 1 1 d .
H7A H 0.0378 0.4870 0.2254 0.074 Uiso 1 1 calc R
C8 C 0.1251(3) 0.41440(12) 0.37079(19) 0.0632(5) Uani 1 1 d .
H8A H 0.1297 0.3617 0.3981 0.076 Uiso 1 1 calc R
C9 C 0.2092(2) 0.47296(12) 0.4633(2) 0.0625(5) Uani 1 1 d .
H9A H 0.2006 0.5248 0.4313 0.075 Uiso 1 1 calc R
C10 C 0.2984(2) 0.46264(11) 0.58956(19) 0.0593(5) Uani 1 1 d .
C11 C 0.3737(3) 0.53403(11) 0.6644(2) 0.0624(5) Uani 1 1 d .
C12 C 0.3235(3) 0.38414(12) 0.6557(2) 0.0664(5) Uani 1 1 d .
C13 C 0.4141(4) 0.32650(17) 0.6168(3) 0.0919(8) Uani 1 1 d .
C14 C 0.5408(3) 0.58310(14) 0.8661(3) 0.0837(7) Uani 1 1 d .
H14A H 0.6033 0.5644 0.9518 0.126 Uiso 1 1 calc R
H14B H 0.4529 0.6185 0.8843 0.126 Uiso 1 1 calc R
H14C H 0.6163 0.6105 0.8156 0.126 Uiso 1 1 calc R
H13B H 0.469(4) 0.3367(17) 0.541(3) 0.103(10) Uiso 1 1 d .
H13A H 0.421(4) 0.278(2) 0.662(3) 0.119(10) Uiso 1 1 d .
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
C11 O2 C14 115.96(17)
C2 C1 C6 121.2(2)
C2 C1 H1A 119.4
C6 C1 H1A 119.4
C3 C2 C1 120.1(2)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C2 C3 C4 119.6(2)
C2 C3 H3A 120.2
C4 C3 H3A 120.2
C3 C4 C5 120.7(2)
C3 C4 H4A 119.6
C5 C4 H4A 119.6
C4 C5 C6 120.8(2)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C5 C6 C1 117.51(19)
C5 C6 C7 123.23(18)
C1 C6 C7 119.25(18)
C8 C7 C6 128.21(19)
C8 C7 H7A 115.9
C6 C7 H7A 115.9
C7 C8 C9 121.76(19)
C7 C8 H8A 119.1
C9 C8 H8A 119.1
C10 C9 C8 128.38(19)
C10 C9 H9A 115.8
C8 C9 H9A 115.8
C9 C10 C12 122.62(17)
C9 C10 C11 117.60(17)
C12 C10 C11 119.78(16)
O1 C11 O2 123.23(18)
O1 C11 C10 124.25(19)
O2 C11 C10 112.51(16)
C13 C12 C10 125.7(2)
C13 C12 Cl1 120.2(2)
C10 C12 Cl1 114.09(16)
C12 C13 H13B 116.4(18)
C12 C13 H13A 120.9(19)
H13B C13 H13A 123(3)
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.750(2)
O1 C11 1.199(2)
O2 C11 1.326(2)
O2 C14 1.448(2)
C1 C2 1.379(3)
C1 C6 1.391(3)
C1 H1A 0.9300
C2 C3 1.365(3)
C2 H2A 0.9300
C3 C4 1.370(3)
C3 H3A 0.9300
C4 C5 1.372(3)
C4 H4A 0.9300
C5 C6 1.387(3)
C5 H5A 0.9300
C6 C7 1.452(3)
C7 C8 1.329(3)
C7 H7A 0.9300
C8 C9 1.435(3)
C8 H8A 0.9300
C9 C10 1.338(3)
C9 H9A 0.9300
C10 C12 1.477(3)
C10 C11 1.488(3)
C12 C13 1.307(3)
C13 H13B 0.94(3)
C13 H13A 0.94(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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 0.2(4)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C1 -0.2(3)
C4 C5 C6 C7 179.5(2)
C2 C1 C6 C5 -0.1(3)
C2 C1 C6 C7 -179.9(2)
C5 C6 C7 C8 -5.1(3)
C1 C6 C7 C8 174.6(2)
C6 C7 C8 C9 178.81(18)
C7 C8 C9 C10 -179.9(2)
C8 C9 C10 C12 -0.3(3)
C8 C9 C10 C11 179.88(19)
C14 O2 C11 O1 1.8(3)
C14 O2 C11 C10 -179.12(18)
C9 C10 C11 O1 1.7(3)
C12 C10 C11 O1 -178.1(2)
C9 C10 C11 O2 -177.37(18)
C12 C10 C11 O2 2.8(3)
C9 C10 C12 C13 68.3(3)
C11 C10 C12 C13 -111.9(3)
C9 C10 C12 Cl1 -109.3(2)
C11 C10 C12 Cl1 70.5(2)
