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_7240693
_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         'C11 H21 N3 O3'
_chemical_formula_sum            'C11 H21 N3 O3'
_chemical_formula_weight         243.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7621(4)
_cell_length_b                   13.2127(4)
_cell_length_c                   21.9038(7)
_cell_measurement_reflns_used    4209
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.0310
_cell_measurement_theta_min      4.5200
_cell_volume                     2825.23(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    SHELXT-2018
_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 0.998
_diffrn_measured_fraction_theta_max 0.988
_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    2.00    --    5.00  19.00 -78.00   50
  2  \w    -22.00  81.00   0.50    2.00    --    0.00  60.00-180.00  206
  3  \w   -179.00  -3.00   0.50   10.00    --  -90.00  60.00   0.00  352
  4  \w    -46.00 -20.00   0.50   10.00    --  -90.00  60.00  60.00   52
  5  \w   -178.00 -66.00   0.50   10.00    --  -90.00  60.00  60.00  224
  6  \w    -73.00  -1.00   0.50   10.00    --  -90.00  60.00  30.00  144
  7  \w   -160.00-134.00   0.50   10.00    --  -90.00  60.00 150.00   52
  8  \w   -111.00 -85.00   0.50   10.00    --  -90.00  60.00 150.00   52
  9  \w    -46.00  -2.00   0.50   10.00    --  -90.00  60.00 150.00   88
 10  \w   -159.00-133.00   0.50   10.00    --  -90.00  60.00  90.00   52
 11  \w   -177.00-151.00   0.50   10.00    --  -90.00  60.00  30.00   52
 12  \w    -58.00  -1.00   0.50   10.00    --  -90.00  57.00 -60.00  114
 13  \w   -173.00-147.00   0.50   10.00    --  -90.00  57.00 -60.00   52
 14  \w   -136.00 -82.00   0.50   10.00    --  -90.00  57.00 -60.00  108
 15  \w   -111.00 -85.00   0.50   10.00    --  -90.00  19.00 -78.00   52
 16  \w   -154.00  -2.00   0.50   10.00    --  -90.00   0.00  60.00  304 
;
_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      0.0287645000
_diffrn_orient_matrix_UB_12      0.1089185000
_diffrn_orient_matrix_UB_13      -0.0216691000
_diffrn_orient_matrix_UB_21      0.1540010000
_diffrn_orient_matrix_UB_22      -0.0245435000
_diffrn_orient_matrix_UB_23      -0.0042684000
_diffrn_orient_matrix_UB_31      -0.0192375000
_diffrn_orient_matrix_UB_32      -0.0336916000
_diffrn_orient_matrix_UB_33      -0.0667453000
_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  0.1546
_diffrn_reflns_av_unetI/netI     0.0994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21112
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.413
_diffrn_reflns_theta_min         3.907
_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    0.689
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 991 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.477
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4634
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.488
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.1390
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3735
_refine_ls_wR_factor_ref         0.3834
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.723
_reflns_number_gt                3726
_reflns_number_total             4634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra07508a2.cif
_cod_data_source_block           shelx_CCDC6
_cod_depositor_comments
'Adding full bibliography for 7240683--7240703.cif.'
_cod_database_code               7240693
_shelx_res_checksum              8269