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_7230682
_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      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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-04-13 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.424(10)
_cell_angle_beta                 95.257(10)
_cell_angle_gamma                109.834(10)
_cell_formula_units_Z            8
_cell_length_a                   10.119(4)
_cell_length_b                   13.630(6)
_cell_length_c                   25.370(9)
_cell_measurement_reflns_used    3014
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.380
_cell_measurement_theta_min      3.033
_cell_volume                     3229(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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.973
_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  0.0596
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29372
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         0.818
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_T_max  0.0206
_exptl_absorpt_correction_T_min  0.0048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1084 before and 0.0644 after correction. The Ratio of minimum to maximum transmission is 0.2330. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_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         1.759
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     829
_refine_ls_number_reflns         14513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0778
_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^)+(0.1080P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9107
_reflns_number_total             14513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00423d2.cif
_cod_data_source_block           mo_2017591_0m
_cod_depositor_comments
'Adding full bibliography for 7230677--7230683.cif.'
_cod_database_code               7230682
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.535
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17C(H17A,H17B), C19C(H19A,H19B), C20C(H20A,H20B), C22C(H22A,H22B), C23C(H23A,
 H23B), C17A(H17C,H17D), C19A(H19C,H19D), C20A(H20C,H20D), C22A(H22C,H22D),
 C23A(H23C,H23D), C17D(H17E,H17F), C19D(H19E,H19F), C20D(H20E,H20F), C22D(H22E,
 H22F), C23D(H23E,H23F), C17B(H17G,H17H), C19B(H19G,H19H), C20B(H20G,H20H),
 C22B(H22G,H22H), C23B(H23G,H23H)
2.b Aromatic/amide H refined with riding coordinates:
 C6C(H6C), C7C(H7C), C8C(H8C), C12C(H12C), C13C(H13C), C15C(H15C), C16C(H16C),
 C6A(H6A), C7A(H7A), C8A(H8A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C6D(H6D), C7D(H7D), C8D(H8D), C12D(H12D), C13D(H13D), C15D(H15D), C16D(H16D),
 C6B(H6B), C7B(H7B), C8B(H8B), C12B(H12B), C13B(H13B), C15B(H15B), C16B(H16B)
;
_olex2_submission_special_instructions 'No special instructions were received'