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_7240695
_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_absolute_configuration syn
_chemical_formula_moiety         'C12 H17 N3 O'
_chemical_formula_sum            'C12 H17 N3 O'
_chemical_formula_weight         219.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 113.349(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7286(3)
_cell_length_b                   13.6712(3)
_cell_length_c                   15.1669(4)
_cell_measurement_reflns_used    37817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.1520
_cell_measurement_theta_min      3.7770
_cell_volume                     2423.14(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -84.00  94.00   0.50    1.50    --    5.00  59.00-180.00  356
  2  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00 -60.00  358
  3  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00-150.00  358
  4  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00   0.00  358
  5  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00 120.00  358
  6  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00 150.00  358
  7  \w   -142.00  37.00   0.50    1.50    --  -52.30  49.00-120.00  358
  8  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00  60.00  358
  9  \w   -142.00  37.00   0.50    1.50    --  -52.30  59.00 120.00  358
 10  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00-122.89  356
 11  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00 177.12  356
 12  \w   -179.00  -1.00   0.50    6.00    --  -90.00  57.00  43.05  356
 13  \w   -179.00  -1.00   0.50    6.00    --  -90.00  55.00-136.20  356
 14  \w   -179.00  -1.00   0.50    6.00    --  -90.00  57.00 -67.92  356
 15  \w   -179.00  -1.00   0.50    6.00    --  -90.00  55.00  28.08  356
 16  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00 156.54  356
 17  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00  55.84  356
 18  \w   -179.00  -1.00   0.50    6.00    --  -90.00  58.00  16.74  356
 19  \w   -179.00  -1.00   0.50    6.00    --  -90.00  58.00 -34.69  356
 20  \w   -179.00  -1.00   0.50    6.00    --  -90.00  57.00  43.05  356
 21  \w   -179.00  -1.00   0.50    6.00    --  -90.00  57.00 -48.00  356
 22  \w   -179.00  -1.00   0.50    6.00    --  -90.00  58.00 -15.88  356
 23  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00  -1.21  356
 24  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00-102.68  356
 25  \w   -179.00  -1.00   0.50    6.00    --  -90.00  59.00-102.68  356
 26  \w   -179.00  -1.00   0.50    6.00    --  -90.00  53.00 131.70  356
 27  \w   -166.00  -1.00   0.50    6.00    --  -90.00  58.00 122.37  330
 28  \w   -137.00  -1.00   0.50    6.00    --  -90.00  57.00-150.86  272
 29  \w   -165.00  -1.00   0.50    6.00    --  -90.00  59.00  88.14  328
 30  \w   -161.00  -1.00   0.50    6.00    --  -90.00  59.00 -88.24  320
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter \c goniometer'
_diffrn_measurement_device_type
;
Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer 
and HyPix 6000 detector
;
_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      -0.0929603000
_diffrn_orient_matrix_UB_12      -0.0629896000
_diffrn_orient_matrix_UB_13      0.0130011000
_diffrn_orient_matrix_UB_21      -0.0925102000
_diffrn_orient_matrix_UB_22      0.0722044000
_diffrn_orient_matrix_UB_23      -0.0623187000
_diffrn_orient_matrix_UB_31      -0.0135512000
_diffrn_orient_matrix_UB_32      -0.0593382000
_diffrn_orient_matrix_UB_33      -0.0904559000
_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  0.0717
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.563
_diffrn_reflns_theta_min         3.856
_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    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.40a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4618
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0622P)^2^+0.4671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4424
_reflns_number_total             4618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra07508a2.cif
_cod_data_source_block           shelx_CCDC8
_cod_depositor_comments
'Adding full bibliography for 7240683--7240703.cif.'
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               7240695
_shelx_res_checksum              13755