Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
Al-Taie, Zahraa S.; Anetts, Simon R.; Christensen, Jeppe; Coles, Simon J.; Horton, Peter N.; Evans, Daniel M.; Jones, Leigh F.; de Kleijne, Frank F. J.; Ledbetter, Shaun M.; Mehdar, Yassin T. H.; Murphy, Patrick J.; Wilson, Jack A.; RSC Advances 10 (2020) 22397–22416; doi:10.1039/C9RA07508A

data_7240698
_publ_section_title
;
 Proline derived guanidine catalysts forge extensive H-bonded
 architectures: a solution and solid state study
;
_journal_issue                   38
_journal_name_full               'RSC Advances'
_journal_page_first              22397
_journal_page_last               22416
_journal_paper_doi               10.1039/C9RA07508A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C14 H20 N4 O3'
_chemical_formula_sum            'C14 H20 N4 O3'
_chemical_formula_weight         292.34
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.889(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4402(4)
_cell_length_b                   12.9330(4)
_cell_length_c                   19.1393(6)
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.6780
_cell_measurement_theta_min      4.1110
_cell_volume                     3033.55(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
Data collection strategy using shutter-less operation of detector. 
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -19.00   6.00   0.50   30.00    --    5.00  47.00 156.00   50
  2  \w    -39.00  -1.00   0.50   30.00    --  -90.00  47.00 156.00   76
  3  \w   -143.00 -47.00   0.50   30.00    --  -90.00  47.00 156.00  192
  4  \w    -88.00  72.00   0.50    5.00    --    0.00  47.00 156.00  320
  5  \w    -33.00   5.00   0.50    5.00    --    0.00  60.00-180.00   76
  6  \w   -178.00  -1.00   0.50   30.00    --  -90.00  29.00  30.00  354
  7  \w    -94.00  -5.00   0.50   30.00    --  -90.00  43.00-150.00  178
  8  \w   -167.00-141.00   0.50   30.00    --  -90.00  60.00  90.00   52
  9  \w   -137.00-110.00   0.50   30.00    --  -90.00  60.00  90.00   54
 10  \w   -136.00 -84.00   0.50   30.00    --  -90.00  29.00 -60.00  104
 11  \w    -82.00  -9.00   0.50   30.00    --  -90.00  60.00  90.00  146
 12  \w    -47.00 -20.00   0.50   30.00    --  -90.00  29.00 -60.00   54
 13  \w   -144.00-108.00   0.50   30.00    --  -90.00  43.00-150.00   72
 14  \w    -54.00 -28.00   0.50   30.00    --  -90.00   0.00-150.00   52
 15  \w   -178.00  -1.00   0.50   30.00    --  -90.00  60.00-120.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter \c goniometer'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0279748000
_diffrn_orient_matrix_UB_12      0.0338948000
_diffrn_orient_matrix_UB_13      -0.0718829000
_diffrn_orient_matrix_UB_21      0.0807771000
_diffrn_orient_matrix_UB_22      0.0805644000
_diffrn_orient_matrix_UB_23      0.0379606000
_diffrn_orient_matrix_UB_31      0.0921807000
_diffrn_orient_matrix_UB_32      -0.0810287000
_diffrn_orient_matrix_UB_33      0.0076636000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.439
_diffrn_reflns_theta_min         4.145
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.1348
_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/[\s^2^(Fo^2^)+54.1975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2896
_refine_ls_wR_factor_ref         0.2952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2357
_reflns_number_total             2837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra07508a2.cif
_cod_data_source_block           2017NCS0681
_cod_depositor_comments
'Adding full bibliography for 7240683--7240703.cif.'
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7240698
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              77869