#------------------------------------------------------------------------------
#$Date: 2017-01-01 01:00:40 +0200 (Sun, 01 Jan 2017) $
#$Revision: 189521 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/39/4513995.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_4513995
loop_
_publ_author_name
'Gao, Yuzhen'
'Zhang, Pengbo'
'Ji, Zhe'
'Tang, Guo'
'Zhao, Yufen'
_publ_section_title
;
 Copper-Catalyzed Cascade Radical Addition--Cyclization Halogen Atom
 Transfer between Alkynes and Unsaturated α-Halogenocarbonyls
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              186
_journal_paper_doi               10.1021/acscatal.6b03033
_journal_year                    2016
_chemical_formula_sum            'C18 H20 Br Cl O4'
_chemical_formula_weight         415.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.405(5)
_cell_angle_beta                 96.467(5)
_cell_angle_gamma                113.588(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6779(5)
_cell_length_b                   9.0204(6)
_cell_length_c                   12.8020(6)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      62.211
_cell_measurement_theta_min      5.35
_cell_volume                     908.37(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4761
_diffrn_reflns_theta_full        62.19
_diffrn_reflns_theta_max         62.19
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    4.599
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.32225
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.939
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1173P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1657
_reflns_number_gt                2614
_reflns_number_total             2813
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b03033_si_002.cif
_cod_data_source_block           t0830
_cod_original_cell_volume        908.37(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.31371(5) 0.77512(5) 0.40130(4) 0.0480(3) Uani 1 1 d .
Cl1A Cl 1.11249(14) 0.93754(13) 0.89086(7) 0.0473(3) Uani 1 1 d .
O4 O 0.6825(3) 0.5701(3) 0.08562(19) 0.0325(6) Uani 1 1 d .
O2 O 0.6242(4) 0.3037(3) 0.2427(2) 0.0364(6) Uani 1 1 d .
O1 O 0.4128(4) 0.3724(3) 0.2775(2) 0.0407(7) Uani 1 1 d .
O3 O 0.9374(3) 0.6332(4) 0.1816(2) 0.0400(7) Uani 1 1 d .
C9 C 0.9521(5) 0.9710(4) 0.7057(3) 0.0304(8) Uani 1 1 d .
H9A H 0.9593 1.0681 0.7383 0.036 Uiso 1 1 calc R
C4 C 0.6143(5) 0.7110(4) 0.2757(3) 0.0264(8) Uani 1 1 d .
H4A H 0.6695 0.7994 0.2338 0.032 Uiso 1 1 calc R
H4B H 0.4937 0.6617 0.2496 0.032 Uiso 1 1 calc R
C7 C 0.8654(4) 0.7757(4) 0.5513(3) 0.0238(7) Uani 1 1 d .
C12 C 0.9332(5) 0.6819(4) 0.6093(3) 0.0289(8) Uani 1 1 d .
H12A H 0.9270 0.5849 0.5773 0.035 Uiso 1 1 calc R
C17 C 0.7537(6) 0.5711(6) -0.0125(3) 0.0404(10) Uani 1 1 d .
H17A H 0.8697 0.6524 -0.0036 0.048 Uiso 1 1 calc R
H17B H 0.6883 0.5995 -0.0684 0.048 Uiso 1 1 calc R
C1 C 0.8055(4) 0.6192(4) 0.3744(3) 0.0246(7) Uani 1 1 d .
H1A H 0.8841 0.5745 0.3900 0.030 Uiso 1 1 calc R
C13 C 0.5555(5) 0.4089(4) 0.2625(2) 0.0258(8) Uani 1 1 d .
C8 C 0.8764(5) 0.9190(4) 0.6018(3) 0.0267(8) Uani 1 1 d .
H8A H 0.8314 0.9825 0.5648 0.032 Uiso 1 1 calc R
C5 C 0.6911(4) 0.5837(4) 0.2695(3) 0.0246(7) Uani 1 1 d .
C3 C 0.6447(4) 0.7740(4) 0.3932(3) 0.0244(7) Uani 1 1 d .
H3A H 0.6873 0.8928 0.4008 0.029 Uiso 1 1 calc R
C2 C 0.7808(4) 0.7214(4) 0.4417(3) 0.0224(7) Uani 1 1 d .
C16 C 0.7886(5) 0.5987(4) 0.1752(3) 0.0259(8) Uani 1 1 d .
C10 C 1.0166(5) 0.8734(5) 0.7592(3) 0.0304(8) Uani 1 1 d .
C15 C 0.4066(8) 0.0671(6) 0.1360(4) 0.0620(15) Uani 1 1 d .
H15A H 0.3354 -0.0460 0.1371 0.093 Uiso 1 1 calc R
H15B H 0.4786 0.0797 0.0823 0.093 Uiso 1 1 calc R
H15C H 0.3371 0.1260 0.1210 0.093 Uiso 1 1 calc R
C11 C 1.0086(5) 0.7301(5) 0.7127(3) 0.0331(9) Uani 1 1 d .
H11A H 1.0533 0.6669 0.7502 0.040 Uiso 1 1 calc R
C14 C 0.5133(6) 0.1316(5) 0.2405(4) 0.0408(10) Uani 1 1 d .
H14A H 0.4404 0.1170 0.2948 0.049 Uiso 1 1 calc R
H14B H 0.5819 0.0707 0.2560 0.049 Uiso 1 1 calc R
C6 C 0.4901(5) 0.7000(5) 0.4493(3) 0.0300(8) Uani 1 1 d .
H6A H 0.5241 0.7286 0.5248 0.036 Uiso 1 1 calc R
H6B H 0.4441 0.5826 0.4365 0.036 Uiso 1 1 calc R
C18 C 0.7510(7) 0.4095(6) -0.0424(3) 0.0504(12) Uani 1 1 d .
H18A H 0.7982 0.4123 -0.1070 0.076 Uiso 1 1 calc R
H18B H 0.6359 0.3293 -0.0522 0.076 Uiso 1 1 calc R
H18C H 0.8170 0.3821 0.0125 0.076 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C16 O4 C17 116.7(3)
C13 O2 C14 116.4(3)
C10 C9 C8 117.7(3)
C3 C4 C5 106.2(3)
C8 C7 C12 117.5(3)
C8 C7 C2 121.1(3)
C12 C7 C2 121.3(3)
C11 C12 C7 121.6(3)
O4 C17 C18 110.6(3)
C2 C1 C5 112.6(3)
O1 C13 O2 125.0(3)
O1 C13 C5 125.0(3)
O2 C13 C5 109.9(3)
C7 C8 C9 122.2(3)
C1 C5 C16 112.4(3)
C1 C5 C13 108.4(3)
C16 C5 C13 108.2(3)
C1 C5 C4 103.1(3)
C16 C5 C4 112.3(3)
C13 C5 C4 112.3(3)
C6 C3 C2 108.5(3)
C6 C3 C4 114.1(3)
C2 C3 C4 103.7(3)
C1 C2 C7 126.5(3)
C1 C2 C3 111.4(3)
C7 C2 C3 122.1(3)
O3 C16 O4 125.5(3)
O3 C16 C5 124.8(3)
O4 C16 C5 109.6(3)
C11 C10 C9 122.3(3)
C11 C10 Cl1A 119.5(3)
C9 C10 Cl1A 118.2(3)
C10 C11 C12 118.7(3)
O2 C14 C15 111.5(4)
C3 C6 Br1 111.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.958(4)
Cl1A C10 1.756(3)
O4 C16 1.333(4)
O4 C17 1.459(5)
O2 C13 1.336(5)
O2 C14 1.460(5)
O1 C13 1.188(5)
O3 C16 1.193(5)
C9 C10 1.384(5)
C9 C8 1.388(5)
C4 C3 1.542(5)
C4 C5 1.544(5)
C7 C8 1.384(5)
C7 C12 1.402(5)
C7 C2 1.472(5)
C12 C11 1.377(5)
C17 C18 1.482(7)
C1 C2 1.331(5)
C1 C5 1.517(4)
C13 C5 1.536(5)
C5 C16 1.530(5)
C3 C6 1.517(5)
C3 C2 1.521(5)
C10 C11 1.373(6)
C15 C14 1.487(7)
