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_7239702
_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.cc20x59f
_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                 91.972(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8479(3)
_cell_length_b                   8.0949(4)
_cell_length_c                   40.0427(14)
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    250
_cell_measurement_theta_max      65.58
_cell_measurement_theta_min      2.21
_cell_volume                     1894.43(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_detector_area_resol_mean 7.9
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_av_unetI/netI     0.1360
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13174
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        65.075
_diffrn_reflns_theta_max         65.075
_diffrn_reflns_theta_min         2.208
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.465
_exptl_absorpt_correction_T_max  0.4681
_exptl_absorpt_correction_T_min  0.2739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       plate
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.075
_refine_diff_density_min         -1.937
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.295
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0901
_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^)+13.6308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2668
_reflns_number_total             3002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01551e2.cif
_cod_data_source_block           1xdiiodox1
_cod_depositor_comments
;Adding full bibliography for 7239700--7239703.cif.

 Adding full bibliography for 7239700--7239703.cif.
;
_cod_database_code               7239702
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.412
_shelx_estimated_absorpt_t_min   0.222
_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. Rigid bond restraints
 C00B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00I(H00G,H00I), C00N(H00N,H00O), C00P(H00Q,H00R)
3.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00M(H00M), C00O(H00P)
3.c Idealised Me refined as rotating group:
 C00L(H00J,H00K,H00L)
;
_olex2_submission_special_instructions 'No special instructions were received'