Mimicking the active site of aldehyde dehydrogenases: stabilization of carbonyl hydrates through hydrogen bonds
A. J. K. Roth; M. Tretbar; C. B. W. Stark; Chem.Commun. 51 (2015) 14175–; doi:10.1039/C5cc02831K

data_7117747
_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 H11 N O2'
_chemical_formula_sum            'C7 H14 Cl3 N O4'
_chemical_formula_weight         282.54
_chemical_melting_point          349.0(10)
_chemical_name_systematic
'4-methylmorpholine 4-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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-18
_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                 91.68
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6911(2)
_cell_length_b                   12.4710(2)
_cell_length_c                   14.9357(2)
_cell_measurement_reflns_used    1
_cell_measurement_temperature    100
_cell_measurement_theta_max      1
_cell_measurement_theta_min      1
_cell_volume                     2362.87(6)
_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 0.958
_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  0.0219
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51329
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.563
_diffrn_reflns_theta_min         2.076
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6971
_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    1.588
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         8934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0280P)^2^+0.8250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0644
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7682
_reflns_number_total             8934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc02831k2.cif
_cod_data_source_block           roth1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '348-350' was changed to '349.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_cell_volume        2362.86(6)
_cod_database_code               7117747
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Me refined with riding coordinates:
 C3(H3A,H3B,H3C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O5(H5), O6(H6)
;
_shelx_res_checksum              27235