Controlling the distance between hydrogen-bonded chloro-s-triazine tapes: crystal engineering using N-alkyl chains and the influence of temperature
Aldilla, Vina Rizki; Bhadbhade, Mohan; Bhattacharyya, Saroj; Kumar, Naresh; Rich, Anne M.; Marjo, Christopher; CrystEngComm  (2017) –; doi:10.1039/C7CE01049D

data_7228722
_publ_section_title
;
 Controlling the distance between hydrogen-bonded chloro-s-triazine tapes:
 crystal engineering using N-alkyl chains and the influence of temperature
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01049D
_journal_year                    2017
_chemical_formula_moiety         'C13 H24 Cl N5'
_chemical_formula_sum            'C13 H24 Cl N5'
_chemical_formula_weight         285.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-19 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                91.51(5)
_cell_angle_beta                 93.57(5)
_cell_angle_gamma                101.03(4)
_cell_formula_units_Z            2
_cell_length_a                   5.120(13)
_cell_length_b                   10.14(3)
_cell_length_c                   17.37(5)
_cell_measurement_reflns_used    343
_cell_measurement_temperature    299.08
_cell_measurement_theta_max      17.308
_cell_measurement_theta_min      2.352
_cell_volume                     883(4)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299.08
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2565
_diffrn_reflns_av_unetI/netI     0.3992
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10162
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.048
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1486 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.6044. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.061
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.3897
_refine_ls_R_factor_gt           0.1323
_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^)+(0.1151P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2354
_refine_ls_wR_factor_ref         0.3686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                712
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01049d2.cif
_cod_data_source_block           vina_bis_pentyl_rt_10july17_0m_a
_cod_database_code               7228722
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C0AA-C6
 2.56 with sigma of 0.02
 C2AA-C14
 2.56 with sigma of 0.02
 C6-C9
 2.56 with sigma of 0.02
 C4-C1AA = C9-C14 = C6-C14 = C6-C2AA = C2AA-C0AA
 1.52 with sigma of 0.02
 C8-C1AA
 1.52 with sigma of 0.02
 C8-C4
 2.56 with sigma of 0.02
 C8-C39
 2.56 with sigma of 0.02
 C20A-C1AA
 2.56 with sigma of 0.02
 C8-C20A
 1.52 with sigma of 0.02
 H20B-H39B
 2.225 with sigma of 0.02
 H14A-H9B
 2.138 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C2AA, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1AA, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8, C20A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20A, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C4(H4A,H4B), C2AA(H2AA,H2AB), C1AA(H1AA,H1AB), C6(H6A,H6B),
 C14(H14A,H14B), C8(H8A,H8B), C20A(H20A,H20B)
4.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5)
4.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              60580
_olex2_submission_special_instructions 'No special instructions were received'