#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503085.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_1503085
loop_
_publ_author_name
'Chen, Zhengwang'
'Li, Jinghao'
'Jiang, Huanfeng'
'Zhu, Shifa'
'Li, Yibiao'
'Qi, Chaorong'
_publ_section_title
;
 Silver-catalyzed difunctionalization of terminal alkynes: highly regio-
 and stereoselective synthesis of (Z)-beta-haloenol acetates.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3262
_journal_page_last               3265
_journal_paper_doi               10.1021/ol101251n
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H13 Br O2'
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 108.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.977(2)
_cell_length_b                   5.5033(11)
_cell_length_c                   13.198(3)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.35
_cell_volume                     688.2(3)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0760
_diffrn_reflns_av_sigmaI/netI    0.1239
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5519
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         3.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.981
_exptl_absorpt_correction_T_max  0.5733
_exptl_absorpt_correction_T_min  0.4683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1777
_refine_ls_R_factor_gt           0.0495
_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)+(0.0625P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                973
_reflns_number_total             2474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101251n_si_001.cif
_cod_data_source_block           2
_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_cell_volume        688.2(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1503085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
Br1 Br -0.01993(11) 1.1198(4) 0.38454(8) 0.0991(5) Uani 1 1 d .
C1 C 0.3157(9) 0.9521(19) -0.1276(7) 0.057(2) Uani 1 1 d .
O1 O 0.1525(7) 0.7605(12) 0.3038(5) 0.0647(18) Uani 1 1 d .
C2 C 0.2769(13) 1.128(4) -0.2051(9) 0.111(4) Uani 1 1 d .
H2 H 0.2158 1.2502 -0.1984 0.133 Uiso 1 1 calc R
C15 C 0.3021(13) 0.554(2) 0.4538(9) 0.090(4) Uani 1 1 d .
H15A H 0.3994 0.5488 0.4970 0.136 Uiso 1 1 calc R
H15B H 0.2801 0.4124 0.4093 0.136 Uiso 1 1 calc R
H15C H 0.2433 0.5585 0.4991 0.136 Uiso 1 1 calc R
C3 C 0.3256(14) 1.132(4) -0.2943(9) 0.122(5) Uani 1 1 d .
H3 H 0.2959 1.2518 -0.3460 0.147 Uiso 1 1 calc R
C4 C 0.4173(13) 0.955(3) -0.3035(10) 0.087(4) Uani 1 1 d .
H4 H 0.4510 0.9531 -0.3617 0.104 Uiso 1 1 calc R
C5 C 0.4583(13) 0.784(3) -0.2271(11) 0.102(4) Uani 1 1 d .
H5 H 0.5219 0.6652 -0.2325 0.122 Uiso 1 1 calc R
C6 C 0.4072(13) 0.782(2) -0.1395(9) 0.090(4) Uani 1 1 d .
H6 H 0.4372 0.6611 -0.0883 0.108 Uiso 1 1 calc R
C7 C 0.2622(9) 0.9536(19) -0.0354(7) 0.058(2) Uani 1 1 d .
C8 C 0.2946(12) 0.773(2) 0.0414(8) 0.078(3) Uani 1 1 d .
H8 H 0.3516 0.6449 0.0340 0.093 Uiso 1 1 calc R
C9 C 0.2460(11) 0.774(2) 0.1287(7) 0.074(3) Uani 1 1 d .
H9 H 0.2695 0.6468 0.1772 0.088 Uiso 1 1 calc R
C10 C 0.1633(9) 0.9621(18) 0.1449(7) 0.054(2) Uani 1 1 d .
C11 C 0.1271(9) 1.137(3) 0.0673(7) 0.068(3) Uani 1 1 d .
H11 H 0.0684 1.2627 0.0742 0.081 Uiso 1 1 calc R
C12 C 0.1740(9) 1.135(3) -0.0218(7) 0.067(3) Uani 1 1 d .
H12 H 0.1456 1.2580 -0.0725 0.080 Uiso 1 1 calc R
C13 C 0.1133(10) 0.9661(19) 0.2369(7) 0.059(3) Uani 1 1 d .
C14 C 0.2773(14) 0.770(3) 0.3875(10) 0.073(3) Uani 1 1 d .
O2 O 0.3502(8) 0.9505(16) 0.3967(6) 0.084(2) Uani 1 1 d .
C16 C 0.0321(8) 1.131(3) 0.2613(6) 0.068(3) Uani 1 1 d .
H16 H -0.0007 1.2595 0.2142 0.082 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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 116.4(9)
C6 C1 C7 122.3(10)
C2 C1 C7 121.4(9)
C14 O1 C13 118.2(9)
C1 C2 C3 122.8(15)
C1 C2 H2 118.6
C3 C2 H2 118.6
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C4 C3 C2 118.8(16)
C4 C3 H3 120.6
C2 C3 H3 120.6
C5 C4 C3 119.0(10)
C5 C4 H4 120.5
C3 C4 H4 120.5
C4 C5 C6 121.3(12)
C4 C5 H5 119.3
C6 C5 H5 119.3
C1 C6 C5 121.7(12)
C1 C6 H6 119.2
C5 C6 H6 119.2
C12 C7 C8 115.9(8)
C12 C7 C1 121.5(9)
C8 C7 C1 122.6(9)
C9 C8 C7 123.0(9)
C9 C8 H8 118.5
C7 C8 H8 118.5
C8 C9 C10 121.1(9)
C8 C9 H9 119.5
C10 C9 H9 119.5
C11 C10 C9 116.1(8)
C11 C10 C13 122.5(9)
C9 C10 C13 121.4(9)
C10 C11 C12 123.2(13)
C10 C11 H11 118.4
C12 C11 H11 118.4
C7 C12 C11 120.6(13)
C7 C12 H12 119.7
C11 C12 H12 119.7
C16 C13 O1 117.9(8)
C16 C13 C10 127.7(10)
O1 C13 C10 114.2(8)
O2 C14 O1 118.2(12)
O2 C14 C15 128.7(13)
O1 C14 C15 113.0(13)
C13 C16 Br1 123.4(10)
C13 C16 H16 118.3
Br1 C16 H16 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C16 1.857(8)
C1 C6 1.349(13)
C1 C2 1.374(17)
C1 C7 1.474(11)
O1 C14 1.383(14)
O1 C13 1.412(11)
C2 C3 1.407(12)
C2 H2 0.9300
C15 C14 1.451(16)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C3 C4 1.365(19)
C3 H3 0.9300
C4 C5 1.345(17)
C4 H4 0.9300
C5 C6 1.402(14)
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.380(14)
C7 C8 1.384(13)
C8 C9 1.382(12)
C8 H8 0.9300
C9 C10 1.380(12)
C9 H9 0.9300
C10 C11 1.369(15)
C10 C13 1.450(12)
C11 C12 1.394(11)
C11 H11 0.9300
C12 H12 0.9300
C13 C16 1.322(14)
C14 O2 1.214(13)
C16 H16 0.9300
