Crystal structure of 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione, C14H15F2NO2
Li, Huixing; Han, Xinlong; Cao, Bin; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 499–501; doi:10.1515/ncrs-2020-0635

data_8104749
_publ_section_title
;
 Crystal structure of
 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione,
 C14H15F2NO2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              499
_journal_page_last               501
_journal_paper_doi               10.1515/ncrs-2020-0635
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H15 F2 N O2'
_chemical_formula_sum            'C14 H15 F2 N O2'
_chemical_formula_weight         267.27
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 114.979(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5474(10)
_cell_length_b                   11.0737(7)
_cell_length_c                   11.4311(10)
_cell_measurement_reflns_used    1402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      3.25
_cell_volume                     1325.0(2)
_computing_cell_refinement       'APEX2-2008 [1]'
_computing_data_collection       'APEX2-2008 [1]'
_computing_data_reduction        'SAINT- 2008 [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7513
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.801
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008 [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.9106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2034
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1886
_reflns_number_total             2688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0635_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104749
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C4A, C5A, C6A, C1A, C12A, O1A, C10A, C13A, C9A, F1A, F2A, C11A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C12, C1, C5, N1, O1, C4, C6, C2, C14, C3, C10, C13, O2, C7, C9, F1, F2, C8, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Others
 Sof(H8B)=Sof(C1A)=Sof(C5A)=Sof(O1A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C4A)=Sof(C13A)=
 Sof(H13A)=Sof(F1A)=Sof(F2A)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C1)=Sof(H8A)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(H6A)=
 Sof(H6B)=Sof(H6C)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(C13)=Sof(H13)=Sof(F1)=Sof(F2)=Sof(O1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8A), C8(H8B), C10(H10), C10A(H10A)
4.d Fitted hexagon refined as free rotating group:
 C3(C7,C8,C9,C10,C4)
4.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C6A(H6AA,H6AB,
 H6AC), C11A(H11D,H11E,H11F)
;