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_7228724
_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         'C11 H20 Cl N5'
_chemical_formula_sum            'C11 H20 Cl N5'
_chemical_formula_weight         257.77
_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   mixed
_audit_creation_date             2017-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-05 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                104.518(5)
_cell_angle_beta                 92.842(6)
_cell_angle_gamma                100.832(5)
_cell_formula_units_Z            2
_cell_length_a                   5.0858(6)
_cell_length_b                   10.0093(10)
_cell_length_c                   15.2007(18)
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      21.577
_cell_measurement_theta_min      2.783
_cell_volume                     731.93(14)
_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      150.0
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10068
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.148
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0999 before and 0.0635 after correction. The Ratio of minimum to maximum transmission is 0.8475. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0678
_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^)+(0.1201P)^2^+0.1829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2093
_refine_ls_wR_factor_ref         0.2561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1250
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01049d2.cif
_cod_data_source_block           partial1_a
_cod_database_code               7228724
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H7C-H11A
 3.826 with sigma of 0.02
 C5-C4 \\sim C5'-C4 \\sim C6'-C5' \\sim C6-C5 \\sim C7-C6 \\sim C7'-C6' \\sim
C9-C8 \\sim C9'-C8 \\sim C9'-
 C10' \\sim C9-C10 \\sim C11-C10 \\sim C11'-C10'
 with sigma of 0.02
 C4-C6 \\sim C5-C7
 with sigma of 0.02
 C4-C6' \\sim C5'-C7'
 with sigma of 0.02
 C8-C10 \\sim C9-C11
 with sigma of 0.02
 C8-C10' \\sim C9'-C11'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7')
Uanis(C11) = Uanis(C11')
4. Rigid body (RIGU) restrains
 C4, H4BD, H4BC, H4AB, H4AA, C5, H5A, H5B, C5', H5'A, H5'B, C6, H6B, H6A, C6',
 H6'A, H6'B, C7, H7A, H7B, H7C, C7', H7'A, H7'B, H7'C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8, H8AB, H8AA, H8BD, H8BC, C9, H9A, H9B, C9', H9'A, H9'B, C10, H10A, H10B,
 C10', H10C, H10D, C11, H11A, H11B, H11C, C11', H11D, H11E, H11F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H4BD(0.5) H4BC(0.5) H4AB(0.5) H4AA(0.5) C5(0.5) H5A(0.5) H5B(0.5)
 C5'(0.5) H5'A(0.5) H5'B(0.5) C6(0.5) H6B(0.5) H6A(0.5) C6'(0.5) H6'A(0.5)
 H6'B(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C7'(0.5) H7'A(0.5) H7'B(0.5)
 H7'C(0.5) H8AB(0.5) H8AA(0.5) H8BD(0.5) H8BC(0.5) C9(0.5) H9A(0.5) H9B(0.5)
 C9'(0.5) H9'A(0.5) H9'B(0.5) C10(0.5) H10A(0.5) H10B(0.5) C10'(0.5) H10C(0.5)
 H10D(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C11'(0.5) H11D(0.5) H11E(0.5)
 H11F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4BD,H4BC), C4(H4AB,H4AA), C5(H5A,H5B), C5'(H5'A,H5'B), C6(H6B,H6A),
 C6'(H6'A,H6'B), C8(H8AB,H8AA), C8(H8BD,H8BC), C9(H9A,H9B), C9'(H9'A,H9'B),
 C10(H10A,H10B), C10'(H10C,H10D)
6.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7'(H7'A,H7'B,H7'C), C11(H11A,H11B,H11C), C11'(H11D,H11E,H11F)
;
_olex2_submission_special_instructions 'No special instructions were received'