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_1560138
_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 H14 N2 O4'
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-10
_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                 102.334(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4514(4)
_cell_length_b                   4.64770(10)
_cell_length_c                   35.6080(8)
_cell_measurement_reflns_used    7469
_cell_measurement_temperature    93
_cell_measurement_theta_max      78.3280
_cell_measurement_theta_min      5.1090
_cell_volume                     2821.46(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.982
_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    -89.00  33.00   0.50   31.53    --    0.00 -77.00 -30.00  244
  2  \w    -27.00  89.00   0.50   31.53    --    0.00  57.00  60.00  232
  3  \w      3.00 121.00   0.50   31.53    --   32.00  66.00 147.13  236
  4  \w     14.00 104.00   0.50   31.53    --   40.00  53.00 -94.96  180
  5  \w     54.00  94.00   0.50   31.53    --   52.00  61.00 -96.06   80
  6  \w     81.00 108.00   0.50   23.43    --  105.20 -82.00  60.00   54
  7  \w     19.00  45.00   0.50   23.43    --  105.20 -82.00  60.00   52
  8  \w     79.00 169.00   0.50   23.43    --  105.20  45.00-120.00  180
  9  \w     73.00 100.00   0.50   23.43    --  105.20 -82.00  30.00   54
 10  \w     76.00 187.00   0.50   23.43    --  105.20  30.00   0.00  222
 11  \w     17.00 134.00   0.50   23.43    --  105.20 -61.00 120.00  234
 12  \w     68.00 114.00   0.50   23.43    --  105.20 -82.00-120.00   92
 13  \w     81.00 109.00   0.50   23.43    --  105.20  45.00-150.00   56
 14  \w     17.00 130.00   0.50   23.43    --  105.20 -61.00 -30.00  226
 15  \w     86.00 160.00   0.50   23.43    --  105.20  45.00 -90.00  148
 16  \w    103.00 135.00   0.50   23.43    --  105.20  75.00  14.57   64
 17  \w     73.00 139.00   0.50   23.43    --  105.20 -82.00 150.00  132
 18  \w     76.00 195.00   0.50   23.43    --  105.20  30.00 -30.00  238
 19  \w     20.00 103.00   0.50   23.43    --  105.20 -82.00 120.00  166
 20  \w    142.00 174.00   0.50   23.43    --  105.20  45.00-150.00   64
 21  \w     85.00 137.00   0.50   23.43    --  105.20 -82.00-180.00  104
 22  \w     17.00 140.00   0.50   23.43    --  105.20 -82.00 -30.00  246
;
_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      0.0360256000
_diffrn_orient_matrix_UB_12      0.2577326000
_diffrn_orient_matrix_UB_13      -0.0172649000
_diffrn_orient_matrix_UB_21      0.0342800000
_diffrn_orient_matrix_UB_22      0.1135109000
_diffrn_orient_matrix_UB_23      0.0407822000
_diffrn_orient_matrix_UB_31      0.0754035000
_diffrn_orient_matrix_UB_32      -0.1748920000
_diffrn_orient_matrix_UB_33      0.0010345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1365
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            16079
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.125
_diffrn_reflns_theta_min         5.086
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method
'Slow evaporation of an EtOAc solution'
_exptl_crystal_size_max          0.733
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0830
_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^)+(0.1820P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2263
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2435
_reflns_number_total             2987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05067a2.cif
_cod_data_source_block           hp-7-40b
_cod_depositor_comments
;
Adding full bibliography for 1560136--1560138.cif.

2022-09-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18.29 H16 N2.29 O4.57'
_cod_original_formula_weight         340.90
_cod_original_formula_moiety         '1.14(C16 H14 N2 O4)'
_cod_original_formula_units_Z            7
_cod_database_code               1560138
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C16 H14 N2 O4'
_chemical_oxdiff_usercomment     HP-7-40b
_reflns_odcompleteness_completeness 99.90
_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 Secondary CH2 refined with riding coordinates:
 C00I(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00c,H00e,H00i)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_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 5.531
_oxdiff_exptl_absorpt_empirical_full_min 0.256