Thermodynamic pathway between the non-polar and ferroelectric polymorphs of guanidinium ethoxysulfonate
Szafrański, Marek; Jarek, Marcin; CrystEngComm  (2020) –; doi:10.1039/D0CE00565G

data_7240536
_publ_section_title
;
 Thermodynamic pathway between the non-polar and ferroelectric polymorphs
 of guanidinium ethoxysulfonate
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00565G
_journal_year                    2020
_chemical_formula_moiety         'C2 H5 O4 S, C H6 N3'
_chemical_formula_sum            'C3 H11 N3 O4 S'
_chemical_formula_weight         185.21
_chemical_name_common            'guanidinium ethoxysulfonate'
_chemical_name_systematic        'guanidinium ethoxysulfonate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                77.442(2)
_cell_angle_beta                 79.666(2)
_cell_angle_gamma                88.939(2)
_cell_formula_units_Z            8
_cell_length_a                   7.8970(2)
_cell_length_b                   14.3744(3)
_cell_length_c                   15.1386(3)
_cell_measurement_reflns_used    10536
_cell_measurement_temperature    300.0(1)
_cell_measurement_theta_max      28.5385
_cell_measurement_theta_min      2.2218
_cell_volume                     1649.76(7)
_computing_cell_refinement       CrysAlisRED
_computing_data_collection       CrysAlisCCD
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300.0(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21720
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.601
_diffrn_reflns_theta_min         2.226
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
The crystal was grown in a glass capillary in the high-temperature phase at 320K and 
then the data were collected at 300K. At this temperature the highly disordered structure results 
in low intensity of the large-angle reflections. Hence the reduced completness of
the data.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.259
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         13981
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1110P)^2^+1.0062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                11105
_reflns_number_total             13981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00565g2.cif
_cod_data_source_block           ges_300
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7240536
_refine_comments
;
 The structure is highly disordered. In the refinenent procedure to keep the refinement stable 
 some of the atoms were left in the single sites, although they showed the substantially 
 elongated thermal elipsoids. This is the reason of the level B alerts in the Checkcif report 
 for atoms O32 and O41. The sulphur atoms have a central position in SO4 groups, 
 and hence their thermal parameters are much smaller than those of the oxygen atoms. 
 The level B alerts in the Checkcif raport indicate that atoms S2, S3 and S4 have their Ueq 
 low when compared to neighbors. But in fact, also the atoms S1 and S5-S8 exhibit 
 nearly isotropic vibrations of small amplitude. 
 The disordered carbon atoms in the ethoxysulfonate groups are responsible for lower 
 precision of C-C bonds (level B alert).
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.59(13) 0.41(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uiso(O14A) = Uiso(O14B)
Uiso(O54A) = Uiso(O54B)
Uiso(C51A) = Uiso(C51B)
Uiso(O64A) = Uiso(O64B)
Uiso(C61A) = Uiso(C61B)
Uiso(C41A) = Uiso(C41B)
Uiso(C42A) = Uiso(C42B)
Uiso(O81A) = Uiso(O81B)
Uiso(O83A) = Uiso(O83B)
Uiso(C81A) = Uiso(C81B)
Uiso(C32A) = Uiso(C32B)
Uiso(C52A) = Uiso(C52B)
Uiso(C62A) = Uiso(C62B)
Uiso(C72A) = Uiso(C72B)
Uiso(C82A) = Uiso(C82B)
4. Others
 Fixed Sof: O14A(0.5) O14B(0.5) C32A(0.5) H32A(0.5) H32B(0.5) H32C(0.5)
 C31A(0.5) H31A(0.5) H31B(0.5) C32B(0.5) H32D(0.5) H32E(0.5) H32F(0.5)
 C31B(0.5) H31C(0.5) H31D(0.5) C42A(0.5) H42A(0.5) H42B(0.5) H42C(0.5)
 C41A(0.5) H41A(0.5) H41B(0.5) C42B(0.5) H42D(0.5) H42E(0.5) H42F(0.5)
 C41B(0.5) H42G(0.5) H42H(0.5) C52A(0.5) H52A(0.5) H52B(0.5) H52C(0.5)
 O54A(0.5) C51A(0.5) H51A(0.5) H51B(0.5) C52B(0.5) H52D(0.5) H52E(0.5)
 H52F(0.5) O54B(0.5) C51B(0.5) H52G(0.5) H52H(0.5) C62A(0.5) H62A(0.5)
 H62B(0.5) H62C(0.5) O64A(0.5) C61A(0.5) H61A(0.5) H61B(0.5) C62B(0.5)
 H62D(0.5) H62E(0.5) H62F(0.5) O64B(0.5) C61B(0.5) H61C(0.5) H61D(0.5)
 O74A(0.5) C71A(0.5) H71A(0.5) H71B(0.5) C72A(0.5) H72A(0.5) H72B(0.5)
 H72C(0.5) O74B(0.5) C71B(0.5) H71C(0.5) H71D(0.5) C72B(0.5) H72D(0.5)
 H72E(0.5) H72F(0.5) C82A(0.5) H82A(0.5) H82B(0.5) H82C(0.5) O81A(0.5)
 O83A(0.5) C81A(0.5) H81A(0.5) H81B(0.5) C82B(0.5) H82D(0.5) H82E(0.5)
 H82F(0.5) O81B(0.5) O83B(0.5) C81B(0.5) H81C(0.5) H81D(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C31A(H31A,H31B), C31B(H31C,H31D), C41A(H41A,
 H41B), C41B(H42G,H42H), C51A(H51A,H51B), C51B(H52G,H52H), C61A(H61A,H61B),
 C61B(H61C,H61D), C71A(H71A,H71B), C71B(H71C,H71D), C81A(H81A,H81B), C81B(H81C,
 H81D)
5.b X=CH2 refined with riding coordinates:
 N15(H15A,H15B), N16(H16A,H16B), N17(H17A,H17B), N25(H25A,H25B), N26(H26A,
 H26B), N27(H27A,H27B), N35(H35A,H35B), N36(H36A,H36B), N37(H37A,H37B),
 N45(H45A,H45B), N46(H46A,H46B), N47(H47A,H47B), N55(H55A,H55B), N56(H56A,H56B),
  N57(H57A,H57B), N65(H65A,H65B), N66(H66A,H66B), N67(H67A,H67B), N75(H75A,
 H75B), N76(H76A,H76B), N77(H77A,H77B), N85(H85A,H85B), N86(H86A,H86B),
 N87(H87A,H87B)
5.c Idealised Me refined with riding coordinates:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C32A(H32A,H32B,H32C), C32B(H32D,
 H32E,H32F), C42A(H42A,H42B,H42C), C42B(H42D,H42E,H42F), C52A(H52A,H52B,H52C),
 C52B(H52D,H52E,H52F), C62A(H62A,H62B,H62C), C62B(H62D,H62E,H62F), C72A(H72A,
 H72B,H72C), C72B(H72D,H72E,H72F), C82A(H82A,H82B,H82C), C82B(H82D,H82E,H82F)
;
_shelx_res_checksum              90782
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'