A missing member of conjugated N-heterocycles: realizing pyrido[1,2-α]azepine by reacting ruthenium alkenylcarbene complex with alkyne.
Zhou, Xiaoxi; Huang, Fanping; Tang, Chun; Zhuo, Qingde; Chen, Zhixin; Zhang, Hong; Xia, Haiping; Chemical communications (Cambridge, England) 54 (2018) 4009–4012; doi:10.1039/c8cc00758f

data_7121414
_publ_section_title
;
 A missing member of conjugated N-heterocycles: realizing
 pyrido[1,2-\a]azepine by reacting ruthenium alkenylcarbene complex with
 alkyne.
;
_journal_issue                   32
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4009
_journal_page_last               4012
_journal_paper_doi               10.1039/c8cc00758f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C16 H18 N, B F4'
_chemical_formula_sum            'C16 H18 B F4 N'
_chemical_formula_weight         311.12
_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     heavy
_audit_creation_date             2014-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-10-02 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.4200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9618(6)
_cell_length_b                   9.9513(4)
_cell_length_c                   13.2243(7)
_cell_measurement_reflns_used    5631
_cell_measurement_temperature    173
_cell_measurement_theta_max      54.92
_cell_measurement_theta_min      6.08
_cell_volume                     1500.19(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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14337
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.040
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4979
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.725
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_refine_ls_extinction_coef       0.005(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1653
_refine_ls_R_factor_gt           0.0982
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2778
_refine_ls_wR_factor_ref         0.3401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1664
_reflns_number_total             3431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00758f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7121414--7121417.cif.'
_cod_database_code               7121414
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F1(0.75) F5(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C16(H16A,H16B), C12(H12A,H12B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C8(H8), C6(H6), C3(H3), C4(H4), C10(H10), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'