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_7240690
_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         'C13 H18 N4 O'
_chemical_formula_sum            'C13 H18 N4 O'
_chemical_formula_weight         246.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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            4
_cell_length_a                   7.98857(9)
_cell_length_b                   11.71525(11)
_cell_length_c                   13.99640(13)
_cell_measurement_reflns_used    15832
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.702321462
_cell_measurement_theta_min      2.19192923429
_cell_volume                     1309.90(2)
_computing_cell_refinement
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_data_reduction
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.0100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_radiation_wavelength_determination estimated
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         36.098
_diffrn_reflns_theta_min         2.821
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CCP4 7.0.040: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 2322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         6422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0826P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                5776
_reflns_number_total             6422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra07508a2.cif
_cod_data_source_block           2017ncs0244
_cod_depositor_comments
'Adding full bibliography for 7240683--7240703.cif.'
_cod_original_cell_volume        1309.91(2)
_cod_database_code               7240690
_shelx_estimated_absorpt_t_min   0.996
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              32867