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_7230677
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-11
_audit_creation_method
;
Olex2 1.2
(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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.8355(3)
_cell_length_b                   15.0442(3)
_cell_length_c                   15.9034(3)
_cell_measurement_reflns_used    8491
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.37
_cell_volume                     3310.20(12)
_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      298.0
_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_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23618
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         1.354
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.945
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2012
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5203
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0307P)^2^+0.2419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0578
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4676
_reflns_number_total             5203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00423d2.cif
_cod_data_source_block           1569122
_cod_depositor_comments
'Adding full bibliography for 7230677--7230683.cif.'
_cod_database_code               7230677
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.593
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.03(3)
 -0.03(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C14B) \\sim Ueq, Uanis(C17B) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O21A) \\sim Ueq, Uanis(I10A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C17A(H17A,H17B), C19A(H19A,H19B), C20A(H20A,H20B), C22A(H22A,H22B), C23A(H23A,
 H23B), C17B(H17C,H17D), C19B(H19C,H19D), C20B(H20C,H20D), C22B(H22C,H22D),
 C23B(H23C,H23D)
4.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C8A(H8A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C6B(H6B), C7B(H7B), C8B(H8B), C12B(H12B), C13B(H13B), C15B(H15B), C16B(H16B)
;
_olex2_submission_special_instructions 'No special instructions were received'