Supramolecular synthesis with N-hetero-tolanes: liquid crystals and hydrogen-bonded and halogen-bonded co-crystals
Flores, Linda; López Duarte, Ismael; Gómez-Lor, Berta; Gutierrez-Puebla, Enrique; Hennrich, Gunther; CrystEngComm 22 (2020) 416–419; doi:10.1039/C9CE01551E

data_7239703
_publ_section_title
;
 Supramolecular synthesis with N-hetero-tolanes: liquid crystals and
 hydrogen-bonded and halogen-bonded co-crystals
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              416
_journal_page_last               419
_journal_paper_doi               10.1039/C9CE01551E
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C3 F2 I, C18 H19 N'
_chemical_formula_sum            'C21 H19 F2 I N'
_chemical_formula_weight         450.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc20x58d
_audit_creation_date             2019-11-14
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-19 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.417(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6232(19)
_cell_length_b                   5.4878(6)
_cell_length_c                   20.948(2)
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      47.52
_cell_measurement_theta_min      2.64
_cell_volume                     1922.2(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      250.0
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_av_unetI/netI     0.1458
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11949
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         2.643
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.270
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.4760
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1266 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.6348.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       0.00044(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0702P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1734
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1684
_reflns_number_total             3274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01551e2.cif
_cod_data_source_block           eg_lf_diiodox2_0m_a
_cod_depositor_comments
;Adding full bibliography for 7239700--7239703.cif.

 Adding full bibliography for 7239700--7239703.cif.
;
_cod_database_code               7239703
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.503
_shelx_estimated_absorpt_t_min   0.350
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00G(H00C,H00D), C00K(H00E,H00G), C00N(H00I,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00F(H00F), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00P(H00Q)
2.c Idealised Me refined as rotating group:
 C00O(H00N,H00O,H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'