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_7228721
_publ_section_title
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 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         'C9 H16 Cl N5'
_chemical_formula_sum            'C9 H16 Cl N5'
_chemical_formula_weight         229.72
_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             2017-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-29 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                93.943(9)
_cell_angle_beta                 96.452(9)
_cell_angle_gamma                100.613(9)
_cell_formula_units_Z            2
_cell_length_a                   5.1163(11)
_cell_length_b                   10.011(2)
_cell_length_c                   12.451(2)
_cell_measurement_reflns_used    1390
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.786
_cell_measurement_theta_min      4.085
_cell_volume                     620.2(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0508
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7336
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.078
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0971 before and 0.0577 after correction. The Ratio of minimum to maximum transmission is 0.7785. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0754
_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^)+(0.1179P)^2^+0.4771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1340
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01049d2.cif
_cod_data_source_block           roomtemp_a
_cod_database_code               7228721
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5A'-C4 \\sim C5A-C4
 with sigma of 0.02
 C8A'-C7 \\sim C8A-C7
 with sigma of 0.02
 C8A-C7 \\sim C8A'-C7 \\sim C8A-C9A \\sim C8A'-C9A'
 with sigma of 0.02
 C5A-C4 \\sim C5A'-C4 \\sim C5A'-C6A' \\sim C5A-C6A
 with sigma of 0.02
3. Rigid bond restraints
 C8A, C8A'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5A, C5A'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6A'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C8A) = Uanis(C9A)
Uanis(C5A') = Uanis(C6A')
Uanis(C5A') = Uanis(C6A)
5. Rigid body (RIGU) restrains
 C4, C5A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C5A', C6A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8A, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8A', C9A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H4BC(0.5) H4BD(0.5) H4AA(0.5) H4AB(0.5) C5A(0.5) H5AA(0.5)
 H5AB(0.5) C5A'(0.5) H5AC(0.5) H5AD(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5)
 C6A'(0.5) H6AD(0.5) H6AE(0.5) H6AF(0.5) H7AA(0.5) H7AB(0.5) H7BC(0.5)
 H7BD(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C8A'(0.5) H8AC(0.5) H8AD(0.5) C9A(0.5)
 H9AA(0.5) H9AB(0.5) H9AC(0.5) C9A'(0.5) H9AD(0.5) H9AE(0.5) H9AF(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C4(H4BC,H4BD), C4(H4AA,H4AB), C5A(H5AA,H5AB), C5A'(H5AC,H5AD), C7(H7AA,H7AB),
 C7(H7BC,H7BD), C8A(H8AA,H8AB), C8A'(H8AC,H8AD)
7.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5)
7.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6A'(H6AD,H6AE,H6AF), C9A(H9AA,H9AB,H9AC), C9A'(H9AD,
 H9AE,H9AF)
;
_olex2_submission_special_instructions 'No special instructions were received'