#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513414.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_1513414
loop_
_publ_author_name
'Liu, Le'
'Zhang-Negrerie, Daisy'
'Du, Yunfei'
'Zhao, Kang'
_publ_section_title
;
 PhICl2 and Wet DMF: An Efficient System for Regioselective
 Chloroformyloxylation/α-Chlorination of Alkenes/α,β-Unsaturated
 Compounds.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              436
_journal_page_last               439
_journal_paper_doi               10.1021/ol403321n
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H16 Cl O4'
_chemical_formula_weight         319.75
_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                 114.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.049(2)
_cell_length_b                   5.3230(11)
_cell_length_c                   13.632(3)
_cell_measurement_reflns_used    2153
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7435
_cell_measurement_theta_min      1.6417
_cell_volume                     795.6(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10126
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_coef       0.101(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0489
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                2297
_reflns_number_total             3759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403321n_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1513414
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.16828(6) 0.21580(15) 0.95413(6) 0.0605(3) Uani 1 1 d . A .
O1 O 1.10454(16) 0.7379(4) 0.73063(13) 0.0528(5) Uani 1 1 d D . .
O2 O 0.91571(17) 0.3982(4) 0.77877(14) 0.0554(6) Uani 1 1 d . . .
O3 O 0.82719(19) 0.2527(5) 0.88315(16) 0.0701(7) Uani 1 1 d . . .
C1 C 1.1509(2) 0.5002(6) 0.7860(2) 0.0452(7) Uani 1 1 d . A .
H1A H 1.1053 0.3606 0.7401 0.054 Uiso 1 1 calc R . .
C2 C 1.2843(3) 0.4756(6) 0.8090(2) 0.0459(7) Uani 1 1 d . . .
C3 C 1.3224(3) 0.2803(6) 0.7642(3) 0.0594(9) Uani 1 1 d . A .
H3A H 1.2662 0.1638 0.7203 0.071 Uiso 1 1 calc R . .
C4 C 1.4446(3) 0.2578(8) 0.7849(3) 0.0754(10) Uani 1 1 d . . .
H4A H 1.4702 0.1253 0.7549 0.090 Uiso 1 1 calc R A .
C5 C 1.5281(3) 0.4287(8) 0.8490(3) 0.0778(12) Uani 1 1 d . A .
H5A H 1.6100 0.4122 0.8622 0.093 Uiso 1 1 calc R . .
C6 C 1.4910(3) 0.6232(8) 0.8933(3) 0.0774(11) Uani 1 1 d . . .
H6A H 1.5475 0.7397 0.9369 0.093 Uiso 1 1 calc R A .
C7 C 1.3696(3) 0.6464(6) 0.8733(2) 0.0606(9) Uani 1 1 d . A .
H7A H 1.3447 0.7795 0.9036 0.073 Uiso 1 1 calc R . .
C8 C 1.0693(14) 0.755(2) 0.6240(6) 0.074(4) Uani 0.49(2) 1 d PDU A 1
H8A H 0.9854 0.8128 0.5926 0.089 Uiso 0.49(2) 1 calc PR A 1
H8B H 1.1181 0.8856 0.6111 0.089 Uiso 0.49(2) 1 calc PR A 1
O4 O 1.0754(13) 0.570(2) 0.5751(5) 0.094(4) Uani 0.49(2) 1 d PDU A 1
C8' C 1.0324(13) 0.711(2) 0.6260(6) 0.070(3) Uani 0.51(2) 1 d PDU A 2
H8'A H 0.9586 0.8020 0.6157 0.085 Uiso 0.51(2) 1 calc PR A 2
H8'B H 1.0716 0.8086 0.5893 0.085 Uiso 0.51(2) 1 calc PR A 2
O4' O 0.9975(17) 0.5260(18) 0.5729(6) 0.114(4) Uani 0.51(2) 1 d PDU A 2
C9 C 1.1238(2) 0.5132(5) 0.8857(2) 0.0431(7) Uani 1 1 d . . .
H9A H 1.1743 0.6456 0.9334 0.052 Uiso 1 1 calc R A .
C10 C 0.9925(2) 0.5651(6) 0.8621(2) 0.0515(8) Uani 1 1 d . A .
H10A H 0.9789 0.5404 0.9267 0.062 Uiso 1 1 calc R . .
H10B H 0.9727 0.7380 0.8389 0.062 Uiso 1 1 calc R . .
C11 C 0.8376(2) 0.2509(7) 0.7990(2) 0.0477(7) Uani 1 1 d . . .
C12 C 0.7673(2) 0.0854(6) 0.7070(2) 0.0485(7) Uani 1 1 d . . .
C13 C 0.7738(3) 0.1041(7) 0.6084(2) 0.0693(10) Uani 1 1 d . . .
H13A H 0.8238 0.2241 0.5979 0.083 Uiso 1 1 calc R . .
C14 C 0.7050(4) -0.0576(9) 0.5250(3) 0.0892(13) Uani 1 1 d . . .
H14A H 0.7094 -0.0465 0.4586 0.107 Uiso 1 1 calc R . .
C15 C 0.6312(3) -0.2326(8) 0.5409(3) 0.0831(12) Uani 1 1 d . . .
H15A H 0.5850 -0.3394 0.4848 0.100 Uiso 1 1 calc R . .
C16 C 0.6245(3) -0.2524(8) 0.6382(3) 0.0741(10) Uani 1 1 d . . .
H16A H 0.5742 -0.3727 0.6484 0.089 Uiso 1 1 calc R . .
C17 C 0.6920(3) -0.0948(6) 0.7208(3) 0.0612(9) Uani 1 1 d . . .
H17A H 0.6872 -0.1087 0.7869 0.073 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'
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
C8' O1 C8 22.2(7)
C8' O1 C1 113.6(6)
C8 O1 C1 120.2(6)
C11 O2 C10 118.5(2)
O1 C1 C2 109.2(2)
O1 C1 C9 104.1(2)
C2 C1 C9 114.9(2)
O1 C1 H1A 109.5
C2 C1 H1A 109.5
C9 C1 H1A 109.5
C3 C2 C7 118.8(3)
C3 C2 C1 119.7(3)
C7 C2 C1 121.5(3)
C2 C3 C4 119.8(3)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 120.7(3)
C5 C4 H4A 119.6
C3 C4 H4A 119.6
C6 C5 C4 119.9(3)
C6 C5 H5A 120.1
C4 C5 H5A 120.1
C5 C6 C7 119.7(4)
C5 C6 H6A 120.1
C7 C6 H6A 120.1
C6 C7 C2 121.1(3)
C6 C7 H7A 119.5
C2 C7 H7A 119.5
O4 C8 O1 118.5(10)
O4 C8 H8A 107.7
O1 C8 H8A 107.7
O4 C8 H8B 107.7
O1 C8 H8B 107.7
H8A C8 H8B 107.1
O4' C8' O1 130.4(11)
O4' C8' H8'A 104.7
O1 C8' H8'A 104.7
O4' C8' H8'B 104.7
O1 C8' H8'B 104.7
H8'A C8' H8'B 105.7
C10 C9 C1 114.3(2)
C10 C9 Cl1 109.4(2)
C1 C9 Cl1 107.07(18)
C10 C9 H9A 108.6
C1 C9 H9A 108.6
Cl1 C9 H9A 108.6
O2 C10 C9 109.4(2)
O2 C10 H10A 109.8
C9 C10 H10A 109.8
O2 C10 H10B 109.8
C9 C10 H10B 109.8
H10A C10 H10B 108.3
O3 C11 O2 123.4(3)
O3 C11 C12 124.3(3)
O2 C11 C12 112.3(2)
C13 C12 C17 119.1(3)
C13 C12 C11 122.6(3)
C17 C12 C11 118.4(3)
C12 C13 C14 119.7(3)
C12 C13 H13A 120.1
C14 C13 H13A 120.1
C15 C14 C13 119.8(3)
C15 C14 H14A 120.1
C13 C14 H14A 120.1
C14 C15 C16 120.8(4)
C14 C15 H15A 119.6
C16 C15 H15A 119.6
C15 C16 C17 119.8(4)
C15 C16 H16A 120.1
C17 C16 H16A 120.1
C16 C17 C12 120.8(3)
C16 C17 H17A 119.6
C12 C17 H17A 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.802(3)
O1 C8' 1.335(7)
O1 C8 1.338(8)
O1 C1 1.461(3)
O2 C11 1.338(3)
O2 C10 1.436(3)
O3 C11 1.205(3)
C1 C2 1.511(4)
C1 C9 1.525(3)
C1 H1A 0.9800
C2 C3 1.377(4)
C2 C7 1.379(4)
C3 C4 1.385(4)
C3 H3A 0.9300
C4 C5 1.369(5)
C4 H4A 0.9300
C5 C6 1.364(5)
C5 H5A 0.9300
C6 C7 1.379(4)
C6 H6A 0.9300
C7 H7A 0.9300
C8 O4 1.211(9)
C8 H8A 0.9700
C8 H8B 0.9700
C8' O4' 1.191(8)
C8' H8'A 0.9700
C8' H8'B 0.9700
C9 C10 1.504(4)
C9 H9A 0.9800
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.478(4)
C12 C13 1.381(4)
C12 C17 1.386(4)
C13 C14 1.393(5)
C13 H13A 0.9300
C14 C15 1.366(6)
C14 H14A 0.9300
C15 C16 1.367(5)
C15 H15A 0.9300
C16 C17 1.368(4)
C16 H16A 0.9300
C17 H17A 0.9300
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
C8' O1 C1 C2 106.6(8)
C8 O1 C1 C2 82.7(8)
C8' O1 C1 C9 -130.2(8)
C8 O1 C1 C9 -154.1(8)
O1 C1 C2 C3 -118.3(3)
C9 C1 C2 C3 125.2(3)
O1 C1 C2 C7 61.0(3)
C9 C1 C2 C7 -55.5(4)
C7 C2 C3 C4 0.5(4)
C1 C2 C3 C4 179.8(3)
C2 C3 C4 C5 -0.4(5)
C3 C4 C5 C6 0.1(5)
C4 C5 C6 C7 0.0(5)
C5 C6 C7 C2 0.1(5)
C3 C2 C7 C6 -0.3(5)
C1 C2 C7 C6 -179.6(3)
C8' O1 C8 O4 -77(2)
C1 O1 C8 O4 1.0(14)
C8 O1 C8' O4' 115(3)
C1 O1 C8' O4' 2.8(15)
O1 C1 C9 C10 54.5(3)
C2 C1 C9 C10 173.8(3)
O1 C1 C9 Cl1 175.87(17)
C2 C1 C9 Cl1 -64.8(3)
C11 O2 C10 C9 123.5(3)
C1 C9 C10 O2 49.0(3)
Cl1 C9 C10 O2 -71.0(3)
C10 O2 C11 O3 0.8(4)
C10 O2 C11 C12 -178.5(2)
O3 C11 C12 C13 174.1(3)
O2 C11 C12 C13 -6.5(4)
O3 C11 C12 C17 -5.8(4)
O2 C11 C12 C17 173.6(3)
C17 C12 C13 C14 -0.1(5)
C11 C12 C13 C14 -180.0(3)
C12 C13 C14 C15 0.4(6)
C13 C14 C15 C16 -0.5(7)
C14 C15 C16 C17 0.3(6)
C15 C16 C17 C12 0.0(5)
C13 C12 C17 C16 -0.1(5)
C11 C12 C17 C16 179.8(3)
