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_7228725
_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         'C7 H11 Cl N5, C4 H7'
_chemical_formula_sum            'C11 H18 Cl N5'
_chemical_formula_weight         255.75
_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             2017-05-12
_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                104.473(14)
_cell_angle_beta                 92.935(15)
_cell_angle_gamma                100.729(13)
_cell_formula_units_Z            2
_cell_length_a                   5.0839(11)
_cell_length_b                   10.0172(19)
_cell_length_c                   15.237(3)
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      20.113
_cell_measurement_theta_min      2.226
_cell_volume                     734.3(3)
_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      149.99
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1032
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19800
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.847
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1458 before and 0.0891 after correction. The Ratio of minimum to maximum transmission is 0.7482. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     197
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.1013
_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^)+(0.1535P)^2^+0.9640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2822
_refine_ls_wR_factor_ref         0.3429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1375
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01049d2.cif
_cod_data_source_block           vina_23nov16_bisbutyl_rt_0m_a
_cod_database_code               7228725
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H7'B-H11A
 3.18 with sigma of 0.02
 C5'-C4' \\sim C4-C5 \\sim C6-C5 \\sim C6'-C5' \\sim C6'-C7' \\sim C6-C7 \\sim
C10-C11 \\sim C10'-C11' ~
 C10'-C9' \\sim C10-C9 \\sim C9'-C8' \\sim C9-C8
 with sigma of 0.02
 N5'-C8' \\sim N4-C4
 with sigma of 0.02
 N1-C1 \\sim N3-C1
 with sigma of 0.02
 N1-C2 \\sim N3-C3
 with sigma of 0.02
 N2-C2 \\sim N2-C3
 with sigma of 0.02
 N5'-C3 \\sim N4-C2
 with sigma of 0.02
3. Restrained planarity
 C2, N1, N3, C3, N2
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7')
Uanis(C6) = Uanis(C6')
Uanis(C10) = Uanis(C11)
Uanis(C11) = Uanis(C11')
5. Rigid body (RIGU) restrains
 C4', C5', C6', C7', C7, C5, C4, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8', C9', C10', C11', C9, C8, C10, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, N5', H5', Cl1, N4, H4, N3, N1, C3, C1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C4'(0.5) C5'(0.5) H5'A(0.5) H5'B(0.5) C6'(0.5) H6'A(0.5) H6'B(0.5)
 C7'(0.5) H7'A(0.5) H7'B(0.5) H7'C(0.5) C8'(0.5) C9'(0.5) H9'A(0.5) H9'B(0.5)
 C10'(0.5) H10C(0.5) H10D(0.5) C11'(0.5) H11D(0.5) H11E(0.5) H11F(0.5) C7(0.5)
 H7A(0.5) H7B(0.5) H7C(0.5) C5(0.5) H5A(0.5) H5B(0.5) C4(0.5) H4A(0.5) H4B(0.5)
 C9(0.5) H9A(0.5) H9B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C8(0.5) H8A(0.5) H8B(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C6'(H6'A,H6'B), C9'(H9'A,H9'B), C10'(H10C,H10D), C5(H5A,H5B),
 C4(H4A,H4B), C9(H9A,H9B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B)
7.b Aromatic/amide H refined with riding coordinates:
 N5'(H5'), N4(H4)
7.c Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C11'(H11D,H11E,H11F), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
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_olex2_submission_special_instructions 'No special instructions were received'