Squaramide-Decorated Covalent Organic Framework as a New Platform for Biomimetic Hydrogen-Bonding Organocatalysis
Li, Xia; Wang, Zhifang; Sun, Jiaxing; Gao, Jia; Zhao, Yu; Peng, Cheng; Aguila, Briana; Ma, Shengqian; Chen, Yao; Zhang, Zhenjie; Chemical Communications  (2019) –; doi:10.1039/C9CC01317B

data_7123237
_publ_section_title
;
 Squaramide-Decorated Covalent Organic Framework as a New Platform for
 Biomimetic Hydrogen-Bonding Organocatalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01317B
_journal_year                    2019
_chemical_formula_moiety         'C16 H14 N4 O2'
_chemical_formula_sum            'C16 H14 N4 O2'
_chemical_formula_weight         294.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-25 deposited with the CCDC.    2019-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.828(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7783(13)
_cell_length_b                   9.7768(7)
_cell_length_c                   10.5658(8)
_cell_measurement_reflns_used    820
_cell_measurement_temperature    117.4(5)
_cell_measurement_theta_max      28.5190
_cell_measurement_theta_min      3.6550
_cell_volume                     1330.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -44.00  61.00   1.00   15.00    --   18.78 -19.00  30.00  105
  2  \w      9.00  39.00   1.00   15.00    --   18.78 -57.00  90.00   30
  3  \w    -83.00 -35.00   1.00   15.00    --  -19.10-178.00  90.00   48
  4  \w     51.00  87.00   1.00   15.00    --   18.78 178.00   0.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0287101000
_diffrn_orient_matrix_UB_12      -0.0318573000
_diffrn_orient_matrix_UB_13      0.0626164000
_diffrn_orient_matrix_UB_21      -0.0436404000
_diffrn_orient_matrix_UB_22      -0.0410842000
_diffrn_orient_matrix_UB_23      -0.0052849000
_diffrn_orient_matrix_UB_31      0.0174641000
_diffrn_orient_matrix_UB_32      -0.0505612000
_diffrn_orient_matrix_UB_33      -0.0349812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2386
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1174
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.847
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+1.6460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                816
_reflns_number_total             1174
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc01317b2.cif
_cod_data_source_block           p170511a
_cod_original_cell_volume        1330.28(19)
_cod_database_code               7123237
_chemical_oxdiff_formula         'C N O'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C1(H1A), C2(H2), C5(H5)
;
_olex2_date_sample_data_collection 2017-05-11
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.331
_oxdiff_exptl_absorpt_empirical_full_min 0.257