Biomimetic hydrogen-bonding cascade for chemical activation: telling a nucleophile from a base.
Park, Hyunchang; Lee, Dongwhan; Chemical science 12 (2020) 590–598; doi:10.1039/d0sc05067a

data_1560137
_publ_section_title
;
 Biomimetic hydrogen-bonding cascade for chemical activation: telling a
 nucleophile from a base.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              590
_journal_page_last               598
_journal_paper_doi               10.1039/d0sc05067a
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C16 H13 Br N2 O4, C H Cl3'
_chemical_formula_sum            'C17 H14 Br Cl3 N2 O4'
_chemical_formula_weight         496.56
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-12 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.121(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.8801(5)
_cell_length_b                   6.94530(10)
_cell_length_c                   23.8077(4)
_cell_measurement_reflns_used    23444
_cell_measurement_temperature    93
_cell_measurement_theta_max      78.8590
_cell_measurement_theta_min      4.1220
_cell_volume                     3842.25(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -26.00  89.00   0.50    3.05    --    0.00  46.00 -15.00  230
  2  \w    -89.00  26.00   0.50    3.05    --    0.00 -46.00-165.00  230
  3  \w     16.00 122.00   0.50    4.93    --  105.20 -46.00-165.00  212
  4  \w    118.00 164.00   0.50    4.93    --  105.20  46.00 -15.00   92
  5  \w    -31.00  -4.00   0.50    3.05    --    0.00 -57.00 -30.00   54
  6  \w    -27.00  26.00   0.50    3.05    --    0.00 -38.00 -60.00  106
  7  \w    -89.00   5.00   0.50    3.05    --    0.00 -38.00  90.00  188
  8  \w     23.00  88.00   0.50    3.05    --    0.00  38.00-150.00  130
  9  \w    -61.00 -35.00   0.50    3.05    --    0.00 -57.00 -30.00   52
 10  \w     41.00  67.00   0.50    4.93    --  105.20 -77.00 -60.00   52
 11  \w     75.00 189.00   0.50    4.93    --  105.20  30.00  30.00  228
 12  \w     80.00 195.00   0.50    4.93    --  105.20  30.00 -60.00  230
 13  \w     70.00 123.00   0.50    4.93    --  105.20  82.00  90.00  106
 14  \w     97.00 138.00   0.50    4.93    --  105.20 -77.00 -60.00   82
 15  \w    148.00 179.00   0.50    4.93    --  105.20  82.00  90.00   62
 16  \w     23.00 128.00   0.50    4.93    --  105.20 -61.00-180.00  210
 17  \w     23.00  60.00   0.50    4.93    --  105.20 -45.00  30.00   74
 18  \w    125.00 189.00   0.50    4.93    --  105.20  77.00-150.00  128
 19  \w     91.00 132.00   0.50    4.93    --  105.20 -45.00   0.00   82
 20  \w     28.00  68.00   0.50    4.93    --  105.20 -45.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0323771000
_diffrn_orient_matrix_UB_12      -0.0016882000
_diffrn_orient_matrix_UB_13      -0.0409805000
_diffrn_orient_matrix_UB_21      0.0474181000
_diffrn_orient_matrix_UB_22      -0.1262142000
_diffrn_orient_matrix_UB_23      0.0489131000
_diffrn_orient_matrix_UB_31      -0.0331208000
_diffrn_orient_matrix_UB_32      -0.1823894000
_diffrn_orient_matrix_UB_33      -0.0335143000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32612
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.235
_diffrn_reflns_theta_min         3.714
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.000
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_recrystallization_method
'Slow evaporation of a Chloroform solution'
_exptl_crystal_size_max          0.832
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.121
_refine_diff_density_max         1.184
_refine_diff_density_min         -1.255
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         8119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0740
_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/[\s^2^(Fo^2^)+(0.0618P)^2^+42.0886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2007
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7707
_reflns_number_total             8119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05067a2.cif
_cod_data_source_block           hp-cyanide_sensor
_cod_depositor_comments
;
Adding full bibliography for 1560136--1560138.cif.

2022-06-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C8 H6.59 Br0.47 Cl1.41 N0.94 O1.88'
_cod_original_formula_weight         233.68
_cod_original_formula_moiety         '0.47(C16 H13 Br N2 O4), 0.47(C H Cl3)'
_cod_original_formula_units_Z            17
_cod_database_code               1560137
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     HP-Cyanide_Sensor
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C00W(H00W), C01C(H01O)
2.b Secondary CH2 refined with riding coordinates:
 C01A(H01A,H01B), C01E(H01J,H01K)
2.c Aromatic/amide H refined with riding coordinates:
 N00I(H00I), C01B(H01C), C01D(H01D), C01F(H01F), C01G(H01G), C012(H012),
 C018(H018), N00J(H00J), C00M(H00M), C00O(H00O), C00Z(H00Z), C013(H013),
 C016(H016), C019(H019)
2.d Idealised Me refined as rotating group:
 C01H(H01E,H01H,H01I), C01I(H01L,H01M,H01N)
2.e Idealised tetrahedral OH refined as rotating group:
 O00B(H00B), O00A(H00A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 20.773
_oxdiff_exptl_absorpt_empirical_full_min 0.293