#------------------------------------------------------------------------------
#$Date: 2017-03-04 06:35:40 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/56/4125646.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_4125646
loop_
_publ_author_name
'Darzi, Evan R.'
'White, Brittany M.'
'Loventhal, Lance K.'
'Zakharov, Lev N.'
'Jasti, Ramesh'
_publ_section_title
;
 An Operationally Simple and Mild Oxidative Homocoupling of Aryl Boronic
 Esters To Access Conformationally Constrained Macrocycles.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3106
_journal_page_last               3114
_journal_paper_doi               10.1021/jacs.6b12658
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C30 H28 Cl2 O4'
_chemical_formula_weight         523.42
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                115.281(7)
_cell_angle_beta                 101.865(8)
_cell_angle_gamma                93.508(8)
_cell_formula_units_Z            1
_cell_length_a                   6.7057(7)
_cell_length_b                   10.4349(10)
_cell_length_c                   10.4710(11)
_cell_measurement_reflns_used    2164
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.50
_cell_measurement_theta_min      4.75
_cell_volume                     639.11(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6284
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.686
_diffrn_reflns_theta_min         4.754
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0599P)²+0.2124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1771
_reflns_number_total             2221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b12658_si_003.cif
_cod_data_source_block           cu_jasti58_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        639.10(12)
_cod_database_code               4125646
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.684
_shelx_estimated_absorpt_t_max   0.927
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
Cl1 Cl 0.67964(11) 0.02142(6) 0.20145(7) 0.0447(2) Uani 1 1 d
O1 O 0.1253(2) 0.81077(15) 0.17497(17) 0.0311(4) Uani 1 1 d
O2 O 0.7573(2) 0.72409(16) 0.45443(17) 0.0311(4) Uani 1 1 d
C1 C 0.0569(3) 0.5527(2) 0.0471(2) 0.0245(5) Uani 1 1 d
C2 C 0.2054(3) 0.6826(2) 0.1629(2) 0.0237(5) Uani 1 1 d
C3 C 0.2197(4) 0.6867(2) 0.3100(2) 0.0256(5) Uani 1 1 d
C4 C 0.3847(4) 0.6660(2) 0.3868(2) 0.0269(5) Uani 1 1 d
C5 C 0.5793(3) 0.6343(2) 0.3378(2) 0.0262(5) Uani 1 1 d
C6 C 0.5762(3) 0.6558(2) 0.2038(2) 0.0237(5) Uani 1 1 d
C7 C 0.4115(3) 0.6769(2) 0.1267(2) 0.0233(5) Uani 1 1 d
C8 C 0.6063(4) 0.4792(2) 0.3037(2) 0.0255(5) Uani 1 1 d
C9 C 0.4376(4) 0.3702(3) 0.2354(3) 0.0349(6) Uani 1 1 d
C10 C 0.4590(4) 0.2295(3) 0.2020(3) 0.0360(6) Uani 1 1 d
C11 C 0.6540(4) 0.1979(2) 0.2386(3) 0.0318(5) Uani 1 1 d
C12 C 0.8263(4) 0.3042(3) 0.3055(3) 0.0320(5) Uani 1 1 d
C13 C 0.8013(4) 0.4451(2) 0.3378(3) 0.0299(5) Uani 1 1 d
C14 C 0.0975(5) 0.8344(3) 0.0494(3) 0.0389(6) Uani 1 1 d
C15 C 0.7594(5) 0.8751(3) 0.5055(3) 0.0443(7) Uani 1 1 d
H3 H 0.104(4) 0.707(2) 0.346(3) 0.027(6) Uiso 1 1 d
H4 H 0.387(4) 0.666(3) 0.478(3) 0.041(7) Uiso 1 1 d
H6 H 0.698(4) 0.647(2) 0.174(2) 0.022(6) Uiso 1 1 d
H7 H 0.414(4) 0.684(2) 0.044(3) 0.021(6) Uiso 1 1 d
H9 H 0.302(4) 0.393(3) 0.212(3) 0.039(7) Uiso 1 1 d
H10 H 0.349(5) 0.158(3) 0.156(3) 0.046(8) Uiso 1 1 d
H12 H 0.962(4) 0.281(2) 0.340(2) 0.017(5) Uiso 1 1 d
H13 H 0.919(4) 0.521(3) 0.387(3) 0.026(6) Uiso 1 1 d
H14A H 0.020(5) 0.739(4) -0.041(4) 0.070(10) Uiso 1 1 d
H14B H 0.233(5) 0.857(3) 0.033(3) 0.051(8) Uiso 1 1 d
H14C H 0.015(5) 0.914(3) 0.066(3) 0.057(9) Uiso 1 1 d
H15A H 0.751(5) 0.901(3) 0.425(4) 0.059(9) Uiso 1 1 d
H15B H 0.647(6) 0.905(4) 0.541(4) 0.069(11) Uiso 1 1 d
H15C H 0.900(4) 0.927(3) 0.585(3) 0.039(7) 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 0.0181 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'
O O 0.0492 0.0322 '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'
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
C14 O1 C2 115.75(17) .
C15 O2 C5 114.63(18) .
C1 C1 C2 177.9(3) 2_565
O1 C2 C1 110.04(17) .
O1 C2 C7 112.97(17) .
C1 C2 C7 108.39(17) .
O1 C2 C3 103.91(16) .
C1 C2 C3 109.65(18) .
C7 C2 C3 111.80(18) .
C4 C3 C2 123.6(2) .
C4 C3 H3 120.5(15) .
C2 C3 H3 116.0(15) .
C3 C4 C5 124.2(2) .
C3 C4 H4 121.4(17) .
C5 C4 H4 114.4(16) .
O2 C5 C4 110.14(18) .
O2 C5 C6 110.17(18) .
C4 C5 C6 111.37(19) .
O2 C5 C8 105.71(17) .
C4 C5 C8 110.22(18) .
C6 C5 C8 109.07(17) .
C7 C6 C5 123.8(2) .
C7 C6 H6 120.6(14) .
C5 C6 H6 115.4(14) .
C6 C7 C2 123.7(2) .
C6 C7 H7 120.9(15) .
C2 C7 H7 115.3(15) .
C9 C8 C13 118.8(2) .
C9 C8 C5 120.4(2) .
C13 C8 C5 120.9(2) .
C8 C9 C10 121.3(2) .
C8 C9 H9 119.4(16) .
C10 C9 H9 119.3(16) .
C9 C10 C11 119.1(2) .
C9 C10 H10 121.4(18) .
C11 C10 H10 119.4(18) .
C12 C11 C10 121.0(2) .
C12 C11 Cl1 119.88(19) .
C10 C11 Cl1 119.07(19) .
C11 C12 C13 118.9(2) .
C11 C12 H12 119.6(12) .
C13 C12 H12 121.1(13) .
C12 C13 C8 120.9(2) .
C12 C13 H13 119.9(14) .
C8 C13 H13 119.1(14) .
O1 C14 H14A 108.4(19) .
O1 C14 H14B 110.5(18) .
H14A C14 H14B 107(3) .
O1 C14 H14C 106.4(18) .
H14A C14 H14C 112(3) .
H14B C14 H14C 113(2) .
O2 C15 H15A 110.7(19) .
O2 C15 H15B 113(2) .
H15A C15 H15B 105(3) .
O2 C15 H15C 106.5(14) .
H15A C15 H15C 110(2) .
H15B C15 H15C 112(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C11 1.740(2) .
O1 C14 1.416(3) .
O1 C2 1.437(2) .
O2 C15 1.429(3) .
O2 C5 1.443(3) .
C1 C1 1.194(4) 2_565
C1 C2 1.494(3) .
C2 C7 1.504(3) .
C2 C3 1.506(3) .
C3 C4 1.315(3) .
C3 H3 0.92(2) .
C4 C5 1.503(3) .
C4 H4 0.95(3) .
C5 C6 1.509(3) .
C5 C8 1.533(3) .
C6 C7 1.317(3) .
C6 H6 0.93(2) .
C7 H7 0.91(2) .
C8 C9 1.379(3) .
C8 C13 1.392(3) .
C9 C10 1.381(3) .
C9 H9 0.97(3) .
C10 C11 1.386(4) .
C10 H10 0.90(3) .
C11 C12 1.380(4) .
C12 C13 1.390(3) .
C12 H12 0.99(2) .
C13 H13 0.96(3) .
C14 H14A 1.04(4) .
C14 H14B 0.99(3) .
C14 H14C 1.00(3) .
C15 H15A 0.98(3) .
C15 H15B 0.92(4) .
C15 H15C 1.05(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 O2 0.99(2) 2.57(2) 3.472(3) 150.7(16) 2_766
C14 H14C Cl1 1.00(3) 2.93(3) 3.748(3) 140(2) 1_465
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
C14 O1 C2 C1 -63.1(2)
C14 O1 C2 C7 58.2(3)
C14 O1 C2 C3 179.58(19)
O1 C2 C3 C4 -131.7(2)
C1 C2 C3 C4 110.7(2)
C7 C2 C3 C4 -9.5(3)
C2 C3 C4 C5 -0.6(3)
C15 O2 C5 C4 -59.5(3)
C15 O2 C5 C6 63.8(3)
C15 O2 C5 C8 -178.5(2)
C3 C4 C5 O2 132.8(2)
C3 C4 C5 C6 10.3(3)
C3 C4 C5 C8 -110.9(2)
O2 C5 C6 C7 -132.6(2)
C4 C5 C6 C7 -10.1(3)
C8 C5 C6 C7 111.8(2)
C5 C6 C7 C2 0.2(3)
O1 C2 C7 C6 126.5(2)
C1 C2 C7 C6 -111.3(2)
C3 C2 C7 C6 9.7(3)
O2 C5 C8 C9 157.9(2)
C4 C5 C8 C9 38.9(3)
C6 C5 C8 C9 -83.6(3)
O2 C5 C8 C13 -23.6(3)
C4 C5 C8 C13 -142.6(2)
C6 C5 C8 C13 94.8(2)
C13 C8 C9 C10 0.7(4)
C5 C8 C9 C10 179.2(2)
C8 C9 C10 C11 0.2(4)
C9 C10 C11 C12 -1.0(4)
C9 C10 C11 Cl1 178.1(2)
C10 C11 C12 C13 0.8(4)
Cl1 C11 C12 C13 -178.23(18)
C11 C12 C13 C8 0.0(3)
C9 C8 C13 C12 -0.8(3)
C5 C8 C13 C12 -179.3(2)
