The crystal structure of 4-((6-fluoropyridin-2-yloxy)methyl)benzonitrile, C13H9FN2O
Lu, Zhi-Qiang; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 659–660; doi:10.1515/ncrs-2022-0177

data_8107180
_publ_section_title
;
 The crystal structure of 4-((6-fluoropyridin-2-yloxy)methyl)benzonitrile,
 C13H9FN2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              659
_journal_page_last               660
_journal_paper_doi               10.1515/ncrs-2022-0177
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C13 H9 F N2 O'
_chemical_formula_sum            'C13 H9 F N2 O'
_chemical_formula_weight         228.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                76.991(8)
_cell_angle_beta                 88.403(9)
_cell_angle_gamma                63.619(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4664(8)
_cell_length_b                   8.2700(7)
_cell_length_c                   10.0709(11)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3090
_cell_measurement_theta_min      2.0720
_cell_volume                     540.93(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -44.00  23.00   0.50    2.56    --   24.18 -39.00  48.00  134
  2  \w    -12.00  32.00   0.50    2.56    --  -23.24 -99.00   0.00   88
  3  \w    -13.00  35.00   0.50    2.56    --  -23.24 -99.00 -90.00   96
  4  \w    -22.00  25.00   0.50    2.56    --  -23.24 -99.00-150.00   94
  5  \w    -14.00  12.00   0.50    2.56    --  -23.24 -99.00-180.00   52
  6  \w    -45.00  15.00   0.50    2.56    --   24.18 -37.00 -90.00  120
  7  \w     -4.00 107.00   0.50    2.56    --   24.18  39.00-157.00  222
  8  \w     44.00  75.00   0.50    2.56    --   24.18 178.00  30.00   62
  9  \w     43.00  68.00   0.50    2.56    --   24.18 178.00  60.00   50
 10  \w    -46.00  -8.00   0.50    2.56    --   24.18  39.00-157.00   76
 11  \w    -62.00  43.00   0.50    2.56    --  -23.24  39.00-157.00  210
 12  \w     45.00 106.00   0.50    2.56    --   24.18-178.00  90.00  122
 13  \w   -111.00 -71.00   0.50    2.56    --  -23.24 -39.00  48.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0952699000
_diffrn_orient_matrix_UB_12      -0.0091633000
_diffrn_orient_matrix_UB_13      -0.0199577000
_diffrn_orient_matrix_UB_21      0.0428295000
_diffrn_orient_matrix_UB_22      -0.0969477000
_diffrn_orient_matrix_UB_23      0.0293216000
_diffrn_orient_matrix_UB_31      -0.0202870000
_diffrn_orient_matrix_UB_32      -0.0151977000
_diffrn_orient_matrix_UB_33      -0.0632705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6733
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.655
_diffrn_reflns_theta_min         2.083
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0913P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1752
_reflns_number_total             2638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0177_suppl.cif
_cod_data_source_block           pei8
_cod_original_cell_volume        540.93(10)
_cod_database_code               8107180
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.971
_diffrn_oxdiff_digest_frames
;
01b850ca0423136766b3b5b4841e6996d600026559c
;
_diffrn_oxdiff_digest_hkl
;
01073bbf192685e3239f9ce772c408c97e559f
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              85926
_shelx_hkl_checksum              28817
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.334
_oxdiff_exptl_absorpt_empirical_full_min 0.577