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_7230679
_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 I N4 O'
_chemical_formula_sum            'C17 H17 I N4 O'
_chemical_formula_weight         420.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 106.02(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.296(3)
_cell_length_b                   7.7220(2)
_cell_length_c                   17.136(2)
_cell_measurement_reflns_used    2363
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.47
_cell_volume                     1691.1(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.986
_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  0.0420
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12889
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.628
_diffrn_reflns_theta_min         1.726
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1185 before and 0.0568 after correction. The Ratio of minimum to maximum transmission is 0.7080. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00423d2.cif
_cod_data_source_block           1823241
_cod_depositor_comments
'Adding full bibliography for 7230677--7230683.cif.'
_cod_original_cell_volume        1691.0(5)
_cod_database_code               7230679
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.804
_shelx_estimated_absorpt_t_min   0.618
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 N1, C2, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C2 \\sim C9: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
4.a Secondary CH2 refined with riding coordinates:
 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), C12(H12), C13(H13), C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'