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_7230681
_publ_section_title
;
 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 Br N4 O'
_chemical_formula_sum            'C17 H17 Br N4 O'
_chemical_formula_weight         373.25
_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                 102.622(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1038(13)
_cell_length_b                   6.8983(6)
_cell_length_c                   25.726(2)
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.512
_cell_measurement_theta_min      2.994
_cell_volume                     3308.3(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_min         1.622
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0623 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.8061. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.521
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0861
_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^)+(0.1606P)^2^+7.6872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2606
_refine_ls_wR_factor_ref         0.2913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1726
_reflns_number_total             2992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00423d2.cif
_cod_data_source_block           1571141(1)
_cod_depositor_comments
'Adding full bibliography for 7230677--7230683.cif.'
_cod_database_code               7230681
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.542
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C23'-C22' = C20'-C19'
 1.56 with sigma of 0.02
 C17-C23
 2.4 with sigma of 0.02
 C19'-C22' = C23'-C20'
 3.1 with sigma of 0.02
 C23-C20
 3 with sigma of 0.02
 N18-O21
 2.8 with sigma of 0.02
 C19-O21
 2.32 with sigma of 0.02
 O21-C23
 2.32 with sigma of 0.02
 N18'-O21'
 2.8 with sigma of 0.02
 C19'-O21'
 2.4 with sigma of 0.02
 O21'-C23'
 2.4 with sigma of 0.02
 O21'-C20' = O21'-C22'
 1.31 with sigma of 0.02
 N18'-C23' = N18'-C19'
 1.46 with sigma of 0.02
 N18-C23 = N18-C19
 1.46 with sigma of 0.02
 C11-C5 \\sim C11'-C5
 with sigma of 0.02
 N18-C17 \\sim N18'-C17'
 with sigma of 0.02
 N18-C23 \\sim N18-C19
 with sigma of 0.02
 C23-C22 \\sim C20-C19 \\sim C20'-C19' \\sim C23'-C22'
 with sigma of 0.02
 O21-C22 \\sim O21'-C20' \\sim O21-C20 \\sim O21'-C22'
 with sigma of 0.02
 C17'-C23' \\sim C17'-C19'
 with sigma of 0.02
3. Rigid bond restraints
 C23, C19', C22'
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C11') \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C12') \\sim Ueq,
Uanis(C15') \\sim Ueq, Uanis(C14') \\sim Ueq, Uanis(C13') \\sim Ueq,
Uanis(C17') \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C22') \\sim Ueq, Uanis(C23') \\sim Ueq, Uanis(O21') \\sim Ueq,
Uanis(C20') \\sim Ueq, Uanis(C19') \\sim Ueq, Uanis(N18') \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O21) \\sim Ueq, Uanis(C20) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(N18) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
5. Others
 Fixed Sof: O21(0.5) O21'(0.5) N18(0.5) N18'(0.5) C12(0.5) H12(0.5) C11(0.5)
 C16(0.5) H16(0.5) C15(0.5) H15(0.5) C14(0.5) C13(0.5) H13(0.5) C17(0.5)
 H17A(0.5) H17B(0.5) C19(0.5) H19A(0.5) H19B(0.5) C20(0.5) H20A(0.5) H20B(0.5)
 C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C12'(0.5) H12'(0.5)
 C11'(0.5) C16'(0.5) H16'(0.5) C15'(0.5) H15'(0.5) C14'(0.5) C13'(0.5)
 H13'(0.5) C17'(0.5) H17C(0.5) H17D(0.5) C19'(0.5) H19C(0.5) H19D(0.5)
 C20'(0.5) H20C(0.5) H20D(0.5) C22'(0.5) H22C(0.5) H22D(0.5) C23'(0.5)
 H23C(0.5) H23D(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,
 H23B), C17'(H17C,H17D), C19'(H19C,H19D), C20'(H20C,H20D), C22'(H22C,H22D),
 C23'(H23C,H23D)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C16(H16), C15(H15), C13(H13), C12'(H12'),
 C16'(H16'), C15'(H15'), C13'(H13')
6.c Fitted hexagon refined as free rotating group:
 C12(C11,C16,C15,C14,C13), C12'(C11',C16',C15',C14',C13')
;
_olex2_submission_special_instructions 'No special instructions were received'