#------------------------------------------------------------------------------
#$Date: 2019-11-04 14:52:53 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/45/4034577.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_4034577
loop_
_publ_author_name
'Al-Smadi, Derar'
'Enugala, Thilak Reddy'
'Kessler, Vadim'
'Mhashal, Anil Ranu'
'Lynn Kamerlin, Shina Caroline'
'Kihlberg, Jan'
'Norberg, Thomas'
'Widersten, Mikael'
_publ_section_title
;
 Chemical and Biochemical Approaches for the Synthesis of Substituted
 Dihydroxybutanones and Di- and Tri-Hydroxypentanones.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6982
_journal_page_last               6991
_journal_paper_doi               10.1021/acs.joc.9b00742
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C11 H13 Cl O3'
_chemical_formula_weight         228.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.694(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.851(15)
_cell_length_b                   4.703(5)
_cell_length_c                   16.195(16)
_cell_measurement_reflns_used    2136
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.64
_cell_volume                     1077.6(19)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 SMART Apex2 CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7459
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         2.229
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.973
_exptl_transmission_factor_min   0.888
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0529
_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)+(0.0289P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1485
_reflns_number_total             1944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00742_si_004.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1077.8(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034577
_shelx_shelxl_version_number     2018/3
_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   0.888
_shelx_estimated_absorpt_t_max   0.973
_exptl_absorpt_special_details   'Bruker SADABS'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.36439(6) 0.14135(16) 0.40950(5) 0.0335(3) Uani 1 1 d . .
O1 O 0.52334(15) 0.6554(4) 0.10437(13) 0.0237(5) Uani 1 1 d . .
O2 O 0.58705(14) 1.1739(4) 0.05900(12) 0.0260(5) Uani 1 1 d . .
H2B H 0.570019 1.319366 0.077843 0.039 Uiso 1 1 calc R U
O3 O 0.75982(16) 0.6505(5) 0.14576(15) 0.0381(6) Uani 1 1 d . .
C5 C 0.3570(2) 0.4900(6) 0.2753(2) 0.0271(7) Uani 1 1 d . .
C7 C 0.5305(2) 0.9929(6) 0.2193(2) 0.0244(7) Uani 1 1 d . .
C4 C 0.4120(2) 0.3906(6) 0.35419(19) 0.0253(7) Uani 1 1 d . .
C9 C 0.6451(2) 1.0115(6) 0.12892(19) 0.0222(6) Uani 1 1 d . .
C8 C 0.5854(2) 0.8282(6) 0.17006(18) 0.0213(6) Uani 1 1 d . .
C2 C 0.5397(2) 0.6822(6) 0.34693(19) 0.0262(7) Uani 1 1 d . .
C1 C 0.4861(2) 0.7884(6) 0.26733(19) 0.0227(6) Uani 1 1 d . .
C10 C 0.7094(2) 0.8204(6) 0.0966(2) 0.0270(7) Uani 1 1 d . .
C6 C 0.3954(2) 0.6908(6) 0.2327(2) 0.0265(7) Uani 1 1 d . .
C3 C 0.5030(2) 0.4798(6) 0.3905(2) 0.0272(7) Uani 1 1 d . .
C11 C 0.7084(3) 0.8445(8) 0.0047(2) 0.0477(10) Uani 1 1 d . .
H11A H 0.664402 0.989482 -0.023807 0.072 Uiso 1 1 calc R U
H11B H 0.770459 0.893543 0.002721 0.072 Uiso 1 1 calc R U
H11C H 0.689662 0.665958 -0.024153 0.072 Uiso 1 1 calc R U
H2A H 0.602(2) 0.747(7) 0.3709(19) 0.022(8) Uiso 1 1 d . .
H8A H 0.628(2) 0.699(7) 0.209(2) 0.025(8) Uiso 1 1 d . .
H3A H 0.543(2) 0.424(6) 0.443(2) 0.020(8) Uiso 1 1 d . .
H7B H 0.479(2) 1.092(7) 0.177(2) 0.025(8) Uiso 1 1 d . .
H5A H 0.289(2) 0.435(6) 0.2502(19) 0.023(8) Uiso 1 1 d . .
H6A H 0.353(2) 0.759(7) 0.175(2) 0.034(9) Uiso 1 1 d . .
H7A H 0.573(2) 1.096(7) 0.258(2) 0.021(8) Uiso 1 1 d . .
H9A H 0.686(2) 1.107(7) 0.174(2) 0.027(8) Uiso 1 1 d . .
H1A H 0.495(2) 0.747(8) 0.059(2) 0.041(11) 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 0.0033 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
C4 C5 C6 118.4(3)
C1 C7 C8 109.6(2)
C5 C4 C3 121.8(3)
C5 C4 Cl1 119.0(2)
C3 C4 Cl1 119.1(2)
O2 C9 C10 109.7(2)
O2 C9 C8 111.1(2)
C10 C9 C8 109.0(2)
O1 C8 C9 109.0(2)
O1 C8 C7 110.7(2)
C9 C8 C7 114.7(2)
C1 C2 C3 121.0(3)
C6 C1 C2 118.4(3)
C6 C1 C7 122.1(3)
C2 C1 C7 119.4(3)
O3 C10 C11 121.6(3)
O3 C10 C9 119.5(3)
C11 C10 C9 119.0(3)
C1 C6 C5 121.6(3)
C4 C3 C2 118.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.750(3)
O1 C8 1.431(3)
O2 C9 1.419(4)
O3 C10 1.213(4)
C5 C4 1.372(4)
C5 C6 1.390(4)
C7 C1 1.510(4)
C7 C8 1.515(4)
C4 C3 1.365(5)
C9 C10 1.516(4)
C9 C8 1.527(4)
C2 C1 1.386(4)
C2 C3 1.391(4)
C1 C6 1.372(4)
C10 C11 1.488(5)
