#------------------------------------------------------------------------------
#$Date: 2015-09-04 11:56:19 +0300 (Fri, 04 Sep 2015) $
#$Revision: 153935 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117748.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_7117748
loop_
_publ_author_name
'A. J. K. Roth'
'M. Tretbar'
'C. B. W. Stark'
_publ_section_title
;
 Mimicking the active site of aldehyde dehydrogenases: stabilization of
 carbonyl hydrates through hydrogen bonds
;
_journal_name_full               Chem.Commun.
_journal_page_first              14175
_journal_paper_doi               10.1039/C5cc02831K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C2 H3 Cl3 O2, C5 H5 N O'
_chemical_formula_sum            'C7 H8 Cl3 N O3'
_chemical_formula_weight         260.49
_chemical_melting_point          ?
_chemical_name_systematic
'pyridine-N-oxide compound with 2,2,2-trichloroethane-1,1-diol (1:1)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2015-05-25 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.56
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.15940(10)
_cell_length_b                   12.8396(2)
_cell_length_c                   13.3985(2)
_cell_measurement_temperature    100
_cell_measurement_theta_max      1.8
_cell_measurement_theta_min      33.5
_cell_volume                     1038.12(3)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'BRUKER AXS SMART APEX'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23617
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.548
_diffrn_reflns_theta_min         2.219
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.7466
_exptl_transmission_factor_min   0.7024
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0214
_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)+(0.0286P)²+0.2949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0588
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                3623
_reflns_number_total             3873
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc02831k2.cif
_cod_data_source_block           roth2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_cell_volume        1038.13(3)
_cod_database_code               7117748
_audit_block_doi                 10.5517/cc1378xj
_shelxl_version_number           2014/6
_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_max   0.874
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13201(3) 0.13963(2) 0.45920(2) 0.02167(5) Uani 1 1 d . . . . .
Cl2 Cl 0.41290(3) 0.18685(2) 0.31743(2) 0.02093(5) Uani 1 1 d . . . . .
Cl3 Cl 0.61057(3) 0.12699(2) 0.52394(2) 0.02052(5) Uani 1 1 d . . . . .
O1 O 0.58096(11) 0.36084(5) 0.46205(5) 0.01796(11) Uani 1 1 d . . . . .
H1 H 0.684(3) 0.3483(12) 0.5080(12) 0.035(4) Uiso 1 1 d . . . . .
O2 O 0.38086(10) 0.31642(5) 0.58296(4) 0.01821(11) Uani 1 1 d . . . . .
H2 H 0.256(3) 0.3282(12) 0.5863(12) 0.037(4) Uiso 1 1 d . . . . .
C1 C 0.39326(12) 0.31190(6) 0.48052(6) 0.01411(13) Uani 1 1 d . . . . .
H1A H 0.264(2) 0.3433(9) 0.4366(9) 0.015(3) Uiso 1 1 d . . . . .
C2 C 0.38939(12) 0.19531(6) 0.44721(6) 0.01442(13) Uani 1 1 d . . . . .
O3 O 0.97032(10) 0.36324(5) 0.59690(5) 0.01823(11) Uani 1 1 d . . . . .
N1 N 0.96811(11) 0.44740(5) 0.65544(5) 0.01413(11) Uani 1 1 d . . . . .
C3 C 0.80695(14) 0.45640(7) 0.71016(6) 0.01826(14) Uani 1 1 d . . . . .
H3 H 0.6990 0.4051 0.7059 0.022 Uiso 1 1 calc R U . . .
C4 C 0.80251(14) 0.54187(7) 0.77255(6) 0.02062(15) Uani 1 1 d . . . . .
H4 H 0.6918 0.5479 0.8103 0.025 Uiso 1 1 calc R U . . .
C5 C 0.96336(15) 0.61868(7) 0.77884(6) 0.02015(15) Uani 1 1 d . . . . .
H5 H 0.9626 0.6762 0.8210 0.024 Uiso 1 1 calc R U . . .
C6 C 1.12562(14) 0.60774(7) 0.72078(7) 0.01973(15) Uani 1 1 d . . . . .
H6 H 1.2343 0.6585 0.7235 0.024 Uiso 1 1 calc R U . . .
C7 C 1.12565(13) 0.52155(6) 0.65909(6) 0.01676(13) Uani 1 1 d . . . . .
H7 H 1.2339 0.5145 0.6201 0.020 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 O2 111.79(6) . .
O1 C1 C2 110.52(6) . .
O2 C1 C2 108.74(6) . .
Cl1 C2 Cl2 108.26(4) . .
Cl3 C2 Cl1 110.23(4) . .
Cl3 C2 Cl2 109.55(4) . .
C1 C2 Cl1 108.85(5) . .
C1 C2 Cl2 109.80(5) . .
C1 C2 Cl3 110.12(5) . .
O3 N1 C3 118.82(7) . .
O3 N1 C7 119.89(6) . .
C3 N1 C7 121.29(7) . .
N1 C3 C4 120.07(8) . .
C3 C4 C5 120.00(8) . .
C4 C5 C6 118.57(8) . .
C7 C6 C5 120.12(8) . .
N1 C7 C6 119.94(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7754(8) .
Cl2 C2 1.7770(8) .
Cl3 C2 1.7667(8) .
O1 C1 1.3810(10) .
O2 C1 1.3912(9) .
C1 C2 1.5609(11) .
O3 N1 1.3369(9) .
N1 C3 1.3521(10) .
N1 C7 1.3532(10) .
C3 C4 1.3832(12) .
C4 C5 1.3884(13) .
C5 C6 1.3911(13) .
C6 C7 1.3813(12) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 Cl1 -173.65(5) . . . .
O1 C1 C2 Cl2 -55.30(7) . . . .
O1 C1 C2 Cl3 65.40(7) . . . .
O2 C1 C2 Cl1 63.29(7) . . . .
O2 C1 C2 Cl2 -178.37(5) . . . .
O2 C1 C2 Cl3 -57.66(7) . . . .
O3 N1 C3 C4 179.03(7) . . . .
O3 N1 C7 C6 -178.97(7) . . . .
N1 C3 C4 C5 0.16(13) . . . .
C3 N1 C7 C6 0.98(12) . . . .
C3 C4 C5 C6 0.51(13) . . . .
C4 C5 C6 C7 -0.46(13) . . . .
C5 C6 C7 N1 -0.28(12) . . . .
C7 N1 C3 C4 -0.92(12) . . . .
