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_7240700
_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         'C11 H15 N3 O'
_chemical_formula_sum            'C11 H15 N3 O'
_chemical_formula_weight         205.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.88050(10)
_cell_length_b                   12.7554(2)
_cell_length_c                   17.4319(2)
_cell_measurement_reflns_used    4519
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.6190
_cell_measurement_theta_min      5.6500
_cell_volume                     2196.94(5)
_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-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 0.999
_diffrn_measured_fraction_theta_max 0.994
_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   -162.00-137.00   0.50    1.76    --  -90.00   0.00   0.00   50
  2  \w    -33.00  -7.00   0.50    1.76    --  -90.00   0.00   0.00   52
  3  \w    -55.00 -15.00   0.50    1.76    --  -90.00  37.00 -24.00   80
  4  \w   -112.00 -63.00   0.50    1.76    --  -90.00  37.00 -24.00   98
  5  \w   -177.00-152.00   0.50    1.76    --  -90.00  37.00 -24.00   50
  6  \w   -179.00-148.00   0.50    1.76    --  -90.00  43.00  90.00   62
  7  \w   -119.00 -90.00   0.50    1.76    --  -90.00  43.00  90.00   58
  8  \w    -66.00 -41.00   0.50    1.76    --  -90.00  43.00  90.00   50
  9  \w    -44.00 -18.00   0.50    1.76    --  -90.00  57.00 125.00   52
 10  \w   -179.00-107.00   0.50    1.76    --  -90.00  57.00 125.00  144
 11  \w   -139.00 -17.00   0.50    1.76    --  -90.00  57.00-150.00  244
 12  \w   -154.00  -1.00   0.50    1.76    --  -90.00  60.00-180.00  306
 13  \w     30.00  65.00   0.50    0.50    --    0.00  57.00 125.00   70
 14  \w    -88.00  12.00   0.50    0.50    --    0.00  57.00 125.00  200
 15  \w     35.00  61.00   0.50    1.76    --    5.00  37.00 -24.00   52
;
_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      -0.1058856000
_diffrn_orient_matrix_UB_12      -0.0831146000
_diffrn_orient_matrix_UB_13      -0.0225389000
_diffrn_orient_matrix_UB_21      -0.0764603000
_diffrn_orient_matrix_UB_22      0.0825051000
_diffrn_orient_matrix_UB_23      -0.0476676000
_diffrn_orient_matrix_UB_31      0.0852585000
_diffrn_orient_matrix_UB_32      -0.0292788000
_diffrn_orient_matrix_UB_33      -0.0709424000
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6642
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.739
_diffrn_reflns_theta_min         5.074
_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    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83306
_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    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0580P)^2^+1.7731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1973
_reflns_number_total             2053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra07508a2.cif
_cod_data_source_block           2017NCS0802
_cod_depositor_comments
'Adding full bibliography for 7240683--7240703.cif.'
_cod_database_code               7240700
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              93599