#------------------------------------------------------------------------------
#$Date: 2018-01-06 04:41:52 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204894 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/80/1548052.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_1548052
loop_
_publ_author_name
'Chen, Xiao-Yang'
'Ozturk, Seyma'
'Sorensen, Erik J.'
_publ_section_title
;
 Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient
 Directing Group.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6280
_journal_page_last               6283
_journal_paper_doi               10.1021/acs.orglett.7b02906
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C7 H4 Cl2 O2'
_chemical_formula_weight         191.00
_chemical_name_common            PDJXC2-44
_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   mixed
_cell_angle_alpha                65.480(2)
_cell_angle_beta                 86.218(2)
_cell_angle_gamma                72.786(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6783(6)
_cell_length_b                   7.8355(7)
_cell_length_c                   8.1648(8)
_cell_measurement_reflns_used    3658
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      31.0100
_cell_measurement_theta_min      2.7479
_cell_volume                     370.51(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5819
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0373P)²+0.1239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                1837
_reflns_number_total             2133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02906_si_002.cif
_cod_data_source_block           PDJXC2a
_cod_depositor_comments          'Adding full bibliography for 1548052.cif.'
_cod_database_code               1548052
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
Cl Cl1 0.36044(6) 0.08891(4) 0.69337(4) 0.01657(10) Uani d . . 1
H H1 0.193(3) 0.646(3) 0.885(3) 0.038(6) Uiso d . . 1
O O1 0.1703(2) 0.73166(16) 0.77940(14) 0.0209(3) Uani d . . 1
C C1 0.2905(2) 0.34241(18) 0.61701(17) 0.0116(3) Uani d . . 1
Cl Cl2 0.18467(6) 0.79792(5) 0.14021(4) 0.01608(10) Uani d . . 1
O O2 0.2624(2) 0.38525(16) 1.04665(14) 0.0241(3) Uani d . . 1
C C2 0.2682(2) 0.45214(18) 0.43239(17) 0.0122(3) Uani d . . 1
H H2 0.290163 0.391521 0.350584 0.015 Uiso calc U R 1
C C3 0.2120(2) 0.65642(19) 0.37135(16) 0.0119(3) Uani d . . 1
C C4 0.1781(2) 0.75122(19) 0.48494(18) 0.0134(3) Uani d . . 1
H H4 0.140045 0.8904 0.437869 0.016 Uiso calc U R 1
C C6 0.2585(2) 0.42915(19) 0.74124(17) 0.0122(3) Uani d . . 1
C C5 0.2014(2) 0.63698(19) 0.67085(18) 0.0134(3) Uani d . . 1
C C7 0.2845(2) 0.3128(2) 0.93653(18) 0.0166(3) Uani d . . 1
H H7 0.320387 0.174009 0.980489 0.02 Uiso calc U R 1
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 O1 H1 107.0(16)
C2 C1 C6 122.50(12)
C2 C1 Cl1 117.23(10)
C6 C1 Cl1 120.27(10)
C1 C2 C3 117.07(12)
C1 C2 H2 121.5
C3 C2 H2 121.5
C4 C3 C2 123.57(12)
C4 C3 Cl2 118.33(10)
C2 C3 Cl2 118.09(10)
C3 C4 C5 118.22(12)
C3 C4 H4 120.9
C5 C4 H4 120.9
C1 C6 C5 117.72(11)
C1 C6 C7 122.46(12)
C5 C6 C7 119.82(12)
O1 C5 C4 117.40(12)
O1 C5 C6 121.67(12)
C4 C5 C6 120.93(12)
O2 C7 C6 123.43(13)
O2 C7 H7 118.3
C6 C7 H7 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7361(13)
O1 C5 1.3450(16)
O1 H1 0.83(2)
C1 C2 1.3827(17)
C1 C6 1.4121(17)
Cl2 C3 1.7359(13)
O2 C7 1.2282(17)
C2 C3 1.3994(17)
C2 H2 0.95
C3 C4 1.3812(18)
C4 C5 1.3966(18)
C4 H4 0.95
C6 C5 1.4185(18)
C6 C7 1.4629(18)
C7 H7 0.95
