Crystal structure and C—H···F hydrogen bonding in the fluorinated bis-benzoxazine: 3,3'-(ethane-1,2-diyl)bis(6-fluoro-3,4-dihydro-2<i>H</i>-1,3-benzoxazine)
Rivera, Augusto; Rojas, Jicli José; Ríos-Motta, Jaime; Bolte, Michael; Acta Crystallographica Section E 72 (2016) 1509–1511; doi:10.1107/S2056989016015243

data_2241861
_publ_section_title
;
 Crystal structure and C---H&#x00B7;&#x00B7;&#x00B7;F hydrogen bonding in
 the fluorinated bis-benzoxazine:
 3,3'-(ethane-1,2-diyl)bis(6-fluoro-3,4-dihydro-2<i>H</i>-1,3-benzoxazine)
;
_journal_coeditor_code           SJ5506
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1509
_journal_page_last               1511
_journal_paper_doi               10.1107/S2056989016015243
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C18 H18 F2 N2 O2'
_chemical_formula_moiety         'C18 H18 F2 N2 O2'
_chemical_formula_sum            'C18 H18 F2 N2 O2'
_chemical_formula_weight         332.34
_chemical_name_common
;
6-Fluoro-3-[2-(6-fluoro-3,4-dihydro-2<i>H</i>-1,3-benzoxazin-3-yl)ethyl]-\
3,4-dihydro-2<i>H</i>-1,3-benzoxazine
;
_chemical_name_systematic
;
3,3'-(Ethane-1,2-diyl)bis(6-fluoro-3,4-dihydro-2<i>H</i>-1,3-benzoxazine)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.473(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0242(6)
_cell_length_b                   6.2316(6)
_cell_length_c                   17.1574(15)
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      3.47
_cell_volume                     750.77(12)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7746
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         3.478
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0538P)^2^+0.1464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                1285
_reflns_number_total             1532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5506sup1.cif
_cod_data_source_block           I
_cod_database_code               2241861
_cod_database_fobs_code          2241861
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.995
_shelx_hkl_checksum              67717
_shelx_res_checksum              51741