#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/57/7105734.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_7105734
loop_
_publ_author_name
'Yanzhao Wang'
'Biao Lu'
'Liming Zhang'
_publ_section_title
;
 The Use of Br/Cl to Promote Regioselective Gold-Catalyzed Rearrangement
 of Propargylic Carboxylates: Efficient Synthesis of (1Z,
 3E)-1-Bromo/Chloro-2-Carboxy-1,3-Dienes from Terminally Halogenated
 Propargyl Carboxylates
;
_journal_name_full               Chem.Commun.
_journal_page_first              9179
_journal_paper_doi               10.1039/c0cc03669b
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C18 H18 Br N O4'
_chemical_formula_weight         392.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 100.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.963(4)
_cell_length_b                   5.3557(7)
_cell_length_c                   20.129(3)
_cell_measurement_temperature    150(2)
_cell_volume                     3387.6(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12990
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.6337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                2892
_reflns_number_total             3428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03669B.TXT
_cod_data_source_block           zm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'multi scan' changed to
'multi-scan' according to
'/home/saulius/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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7105734
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.203764(8) 0.97546(5) 0.501725(12) 0.03386(13) Uani 1 1 d . . .
C1 C 0.15341(7) 0.9795(4) 0.53764(12) 0.0252(5) Uani 1 1 d . . .
H1 H 0.1341 1.1092 0.5261 0.030 Uiso 1 1 calc R . .
C2 C 0.14475(7) 0.8017(4) 0.57906(10) 0.0222(4) Uani 1 1 d . . .
C3 C 0.20470(7) 0.6225(4) 0.64721(10) 0.0211(4) Uani 1 1 d . . .
C4 C 0.23314(7) 0.4008(4) 0.65397(12) 0.0277(5) Uani 1 1 d . . .
H4A H 0.2525 0.4150 0.6229 0.041 Uiso 1 1 calc R . .
H4B H 0.2163 0.2523 0.6441 0.041 Uiso 1 1 calc R . .
H4C H 0.2490 0.3919 0.6993 0.041 Uiso 1 1 calc R . .
C5 C 0.10712(7) 0.7963(4) 0.60987(10) 0.0244(5) Uani 1 1 d . . .
H5 H 0.0887 0.9319 0.6022 0.029 Uiso 1 1 calc R . .
C6 C 0.09695(7) 0.6113(4) 0.64839(11) 0.0248(5) Uani 1 1 d . . .
H6 H 0.1151 0.4740 0.6549 0.030 Uiso 1 1 calc R . .
C7 C 0.05891(7) 0.6059(4) 0.68201(11) 0.0278(5) Uani 1 1 d . . .
H7A H 0.0430 0.7597 0.6718 0.033 Uiso 1 1 calc R . .
H7B H 0.0684 0.5981 0.7306 0.033 Uiso 1 1 calc R . .
C8 C 0.02943(7) 0.3844(4) 0.65965(11) 0.0245(5) Uani 1 1 d . . .
H8A H 0.0451 0.2303 0.6705 0.029 Uiso 1 1 calc R . .
H8B H 0.0062 0.3863 0.6846 0.029 Uiso 1 1 calc R . .
C9 C 0.01130(7) 0.3900(4) 0.58445(10) 0.0229(4) Uani 1 1 d . . .
H9A H 0.0344 0.3672 0.5598 0.027 Uiso 1 1 calc R . .
H9B H -0.0009 0.5536 0.5729 0.027 Uiso 1 1 calc R . .
C10 C -0.02253(7) 0.1930(4) 0.56121(10) 0.0229(5) Uani 1 1 d . . .
H10A H -0.0316 0.2052 0.5126 0.028 Uiso 1 1 calc R . .
H10B H -0.0103 0.0285 0.5713 0.028 Uiso 1 1 calc R . .
C11 C -0.06815(7) 0.0632(4) 0.64495(11) 0.0222(5) Uani 1 1 d . . .
C12 C -0.10766(7) 0.1638(4) 0.66429(10) 0.0215(4) Uani 1 1 d . . .
C13 C -0.13038(7) 0.0806(4) 0.71200(11) 0.0260(5) Uani 1 1 d . . .
H13 H -0.1217 -0.0589 0.7385 0.031 Uiso 1 1 calc R . .
C14 C -0.16663(7) 0.2126(4) 0.71902(12) 0.0294(5) Uani 1 1 d . . .
H14 H -0.1827 0.1603 0.7506 0.035 Uiso 1 1 calc R . .
C15 C -0.17936(8) 0.4215(5) 0.67963(13) 0.0319(5) Uani 1 1 d . . .
H15 H -0.2036 0.5081 0.6857 0.038 Uiso 1 1 calc R . .
C16 C -0.15646(8) 0.5038(4) 0.63119(14) 0.0288(5) Uani 1 1 d . . .
H16 H -0.1652 0.6423 0.6043 0.035 Uiso 1 1 calc R . .
C17 C -0.12045(7) 0.3722(4) 0.62468(10) 0.0218(4) Uani 1 1 d . . .
C18 C -0.08941(7) 0.4109(4) 0.57871(11) 0.0217(4) Uani 1 1 d . . .
N N -0.05944(5) 0.2209(3) 0.59378(8) 0.0209(4) Uani 1 1 d . . .
O1 O 0.17220(5) 0.5972(3) 0.59312(7) 0.0226(3) Uani 1 1 d . . .
O2 O 0.20871(5) 0.8028(3) 0.68275(8) 0.0305(4) Uani 1 1 d . . .
O3 O -0.04703(5) -0.1159(3) 0.66685(8) 0.0316(4) Uani 1 1 d . . .
O4 O -0.08905(5) 0.5703(3) 0.53613(8) 0.0287(4) Uani 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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br 121.65(17) . . ?
C2 C1 H1 119.2 . . ?
Br C1 H1 119.2 . . ?
C1 C2 O1 119.5(2) . . ?
C1 C2 C5 124.6(2) . . ?
O1 C2 C5 115.84(18) . . ?
O2 C3 O1 122.6(2) . . ?
O2 C3 C4 126.5(2) . . ?
O1 C3 C4 110.90(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 124.9(2) . . ?
C6 C5 H5 117.5 . . ?
C2 C5 H5 117.5 . . ?
C5 C6 C7 125.6(2) . . ?
C5 C6 H6 117.2 . . ?
C7 C6 H6 117.2 . . ?
C6 C7 C8 112.92(18) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 112.32(18) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 114.37(17) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N C10 C9 112.23(17) . . ?
N C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 N 125.1(2) . . ?
O3 C11 C12 129.5(2) . . ?
N C11 C12 105.46(17) . . ?
C13 C12 C17 121.4(2) . . ?
C13 C12 C11 130.2(2) . . ?
C17 C12 C11 108.39(18) . . ?
C12 C13 C14 117.6(2) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 117.4(2) . . ?
C17 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C16 C17 C12 121.4(2) . . ?
C16 C17 C18 130.7(2) . . ?
C12 C17 C18 107.98(19) . . ?
O4 C18 N 125.0(2) . . ?
O4 C18 C17 129.1(2) . . ?
N C18 C17 105.84(18) . . ?
C18 N C11 112.34(17) . . ?
C18 N C10 123.92(17) . . ?
C11 N C10 123.73(17) . . ?
C3 O1 C2 116.14(16) . . ?
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
Br C1 1.881(2) . ?
C1 C2 1.328(3) . ?
C1 H1 0.9300 . ?
C2 O1 1.399(2) . ?
C2 C5 1.451(3) . ?
C3 O2 1.195(3) . ?
C3 O1 1.367(2) . ?
C3 C4 1.486(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.334(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.496(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.519(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.522(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N 1.458(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.209(3) . ?
C11 N 1.399(3) . ?
C11 C12 1.489(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.389(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.490(3) . ?
C18 O4 1.211(3) . ?
C18 N 1.392(3) . ?
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
Br C1 C2 O1 -4.3(3) . . . . ?
Br C1 C2 C5 178.41(16) . . . . ?
C1 C2 C5 C6 175.9(2) . . . . ?
O1 C2 C5 C6 -1.5(3) . . . . ?
C2 C5 C6 C7 178.3(2) . . . . ?
C5 C6 C7 C8 120.5(2) . . . . ?
C6 C7 C8 C9 -61.6(3) . . . . ?
C7 C8 C9 C10 -172.58(19) . . . . ?
C8 C9 C10 N 60.9(2) . . . . ?
O3 C11 C12 C13 0.2(4) . . . . ?
N C11 C12 C13 179.9(2) . . . . ?
O3 C11 C12 C17 -179.7(2) . . . . ?
N C11 C12 C17 0.0(2) . . . . ?
C17 C12 C13 C14 0.1(3) . . . . ?
C11 C12 C13 C14 -179.7(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C12 0.7(3) . . . . ?
C15 C16 C17 C18 -179.8(2) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C11 C12 C17 C16 179.6(2) . . . . ?
C13 C12 C17 C18 -179.85(19) . . . . ?
C11 C12 C17 C18 0.0(2) . . . . ?
C16 C17 C18 O4 0.1(4) . . . . ?
C12 C17 C18 O4 179.6(2) . . . . ?
C16 C17 C18 N -179.6(2) . . . . ?
C12 C17 C18 N -0.1(2) . . . . ?
O4 C18 N C11 -179.6(2) . . . . ?
C17 C18 N C11 0.1(2) . . . . ?
O4 C18 N C10 1.9(3) . . . . ?
C17 C18 N C10 -178.45(17) . . . . ?
O3 C11 N C18 179.6(2) . . . . ?
C12 C11 N C18 -0.1(2) . . . . ?
O3 C11 N C10 -1.8(3) . . . . ?
C12 C11 N C10 178.46(17) . . . . ?
C9 C10 N C18 72.7(2) . . . . ?
C9 C10 N C11 -105.7(2) . . . . ?
O2 C3 O1 C2 3.4(3) . . . . ?
C4 C3 O1 C2 -176.15(18) . . . . ?
C1 C2 O1 C3 89.7(2) . . . . ?
C5 C2 O1 C3 -92.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653234
