Choice of hydrogen bonds or halogen bonds by 2-halogenated 5-morpholinomethylphenyl triazolo[1,5-a]pyridine
Li, Changfu; Chai, Yingying; Zhou, Xinglong; Shen, Zhen; Ma, Beibei; Chen, Bojiang; Huang, Ridong; Chen, Hai; Li, Weimin; He, Yang; CrystEngComm 20 (2018) 3006–; doi:10.1039/C8CE00423D

data_7230683
_publ_section_title
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 Choice of hydrogen bonds or halogen bonds by 2-halogenated
 5-morpholinomethylphenyl triazolo[1,5-a]pyridine
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3006
_journal_paper_doi               10.1039/C8CE00423D
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C17 H17 Cl N4 O'
_chemical_formula_sum            'C17 H17 Cl N4 O'
_chemical_formula_weight         328.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2018-04-26 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.145(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.928(5)
_cell_length_b                   6.9102(17)
_cell_length_c                   25.591(7)
_cell_measurement_reflns_used    1409
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.77
_cell_measurement_theta_min      2.43
_cell_volume                     3259.5(15)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8456
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.634
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0691 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8926. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0981P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1961
_reflns_number_total             2945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00423d2.cif
_cod_data_source_block           1828638(1)
_cod_depositor_comments
'Adding full bibliography for 7230677--7230683.cif.'
_cod_original_cell_volume        3259.7(14)
_cod_database_code               7230683
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O21') \\sim Ueq, Uanis(N18') \\sim Ueq, Uanis(C11') \\sim Ueq,
Uanis(C16') \\sim Ueq, Uanis(C15') \\sim Ueq, Uanis(C14') \\sim Ueq,
Uanis(C13') \\sim Ueq, Uanis(C12') \\sim Ueq, Uanis(C17') \\sim Ueq,
Uanis(C20') \\sim Ueq, Uanis(C22') \\sim Ueq, Uanis(C23') \\sim Ueq,
Uanis(C19') \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(N18) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(O21) \\sim Ueq, Uanis(C22) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C11)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(C13)=Sof(H13)=
 Sof(C12)=Sof(H12)=1-FVAR(1)
 Sof(C11')=Sof(C16')=Sof(H16')=Sof(C15')=Sof(H15')=Sof(C14')=Sof(C13')=
 Sof(H13')=Sof(C12')=Sof(H12')=FVAR(1)
 Sof(C17)=Sof(H17C)=Sof(H17D)=1-FVAR(2)
 Sof(C17')=Sof(H17A)=Sof(H17B)=FVAR(2)
 Sof(O21)=Sof(N18)=Sof(C19)=Sof(H19C)=Sof(H19D)=Sof(C20)=Sof(H20C)=Sof(H20D)=
 Sof(C22)=Sof(H22C)=Sof(H22D)=Sof(C23)=Sof(H23C)=Sof(H23D)=1-FVAR(3)
 Sof(O21')=Sof(N18')=Sof(C19')=Sof(H19A)=Sof(H19B)=Sof(C20')=Sof(H20A)=
 Sof(H20B)=Sof(C22')=Sof(H22A)=Sof(H22B)=Sof(C23')=Sof(H23A)=Sof(H23B)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C17(H17C,H17D), C19(H19C,H19D), C20(H20C,H20D), C22(H22C,H22D), C23(H23C,
 H23D), C17'(H17A,H17B), C19'(H19A,H19B), C20'(H20A,H20B), C22'(H22A,H22B),
 C23'(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C16(H16), C15(H15), C13(H13), C12(H12), C16'(H16'),
 C15'(H15'), C13'(H13'), C12'(H12')
4.c Fitted hexagon refined as free rotating group:
 C11(C16,C15,C14,C13,C12), C11'(C16',C15',C14',C13',C12')
;
_olex2_submission_special_instructions 'No special instructions were received'