Difluoromethane as a precursor to difluoromethyl borates
Geri, Jacob B.; Aguilera, Ellen Y.; Szymczak, Nathaniel K.; Chemical Communications  (2019) –; doi:10.1039/C9CC01565E

data_7123287
_publ_section_title
;
 Difluoromethane as a precursor to difluoromethyl borates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01565E
_journal_year                    2019
_chemical_formula_moiety         'C23 H51 B3 F2 K N3 O7'
_chemical_formula_sum            'C23 H51 B3 F2 K N3 O7'
_chemical_formula_weight         591.19
_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     iterative
_audit_creation_date             2019-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-02-18 deposited with the CCDC.    2019-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0781(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.78950(11)
_cell_length_b                   13.33093(19)
_cell_length_c                   26.4981(4)
_cell_measurement_reflns_used    13713
_cell_measurement_temperature    90
_cell_measurement_theta_max      66.3740
_cell_measurement_theta_min      3.3230
_cell_volume                     3104.84(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      90
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -110.00  70.00   1.00    1.00    --  -20.00   0.00-180.00  180
  2  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  3  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  4  \w    -25.00  43.00   1.00    1.00    --  -20.00  36.00 120.00   68
  5  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00-180.00   45
  6  \w   -173.00-128.00   1.00    4.00    --  -92.00 -36.00 120.00   45
  7  \w   -133.00 -88.00   1.00    4.00    --  -92.00 -36.00 -60.00   45
  8  \w   -104.00 -59.00   1.00    4.00    --  -92.00  36.00  60.00   45
  9  \w   -122.00 -77.00   1.00    4.00    --  -92.00 -72.00  60.00   45
 10  \w   -174.00 -78.00   1.00    4.00    --  -92.00 -72.00-120.00   96
 11  \w    -93.00 -35.00   1.00    4.00    --  -92.00  36.00-120.00   58
 12  \w   -176.00 -77.00   1.00    4.00    --  -92.00 -72.00 -60.00   99
 13  \w   -147.00 -75.00   1.00    4.00    --  -92.00 -72.00-180.00   72
 14  \w   -176.00 -77.00   1.00    4.00    --  -92.00 -72.00 120.00   99
 15  \w   -177.00-116.00   1.00    4.00    --  -92.00 -36.00  60.00   61
 16  \w    -87.00  -9.00   1.00    4.00    --  -92.00  36.00 -60.00   78
 17  \w   -102.00 -14.00   1.00    4.00    --  -92.00  36.00   0.00   88
 18  \w   -102.00 -21.00   1.00    4.00    --  -92.00  72.00 120.00   81
 19  \w   -175.00-104.00   1.00    4.00    --  -92.00 -36.00   0.00   71
 20  \w   -104.00 -52.00   1.00    4.00    --  -92.00  72.00  60.00   52
 21  \w   -109.00 -14.00   1.00    4.00    --  -92.00  72.00-120.00   95
 22  \w   -105.00 -24.00   1.00    4.00    --  -92.00  36.00-120.00   81
 23  \w   -105.00  -2.00   1.00    4.00    --  -92.00  36.00-180.00  103
 24  \w   -106.00  -2.00   1.00    4.00    --  -92.00  72.00 -60.00  104
 25  \w   -106.00  -2.00   1.00    4.00    --  -92.00  72.00 -60.00  104
 26  \w   -107.00 -29.00   1.00    4.00    --  -92.00  72.00   0.00   78
 27  \w   -117.00 -72.00   1.00    4.00    --  -92.00  72.00 180.00   45
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0929750000
_diffrn_orient_matrix_UB_12      -0.0611690000
_diffrn_orient_matrix_UB_13      -0.0384602000
_diffrn_orient_matrix_UB_21      0.0541633000
_diffrn_orient_matrix_UB_22      -0.0700981000
_diffrn_orient_matrix_UB_23      0.0426273000
_diffrn_orient_matrix_UB_31      -0.1383402000
_diffrn_orient_matrix_UB_32      -0.0685131000
_diffrn_orient_matrix_UB_33      -0.0092570000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            46752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.191
_diffrn_reflns_theta_min         3.336
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0803
_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^)+(0.1210P)^2^+5.9254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2319
_refine_ls_wR_factor_ref         0.2364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5268
_reflns_number_total             5778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01565e2.cif
_cod_data_source_block           ea552
_cod_original_cell_volume        3104.83(7)
_cod_database_code               7123287
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H43B3F2KN3O6
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.07
_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.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C19(H19A,H19B), C9(H9A,H9B),
 C16(H16A,H16B), C10(H10A,H10B), C11(H11A,H11B), C17(H17A,H17B), C14(H14A,H14B),
  C15(H15A,H15B), C18(H18A,H18B), C21(H21A,H21B), C20(H20A,H20B), C23(H23A,
 H23B), C22(H22A,H22B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C7(H7A,
 H7B,H7C), C6(H6A,H6B,H6C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.723