#------------------------------------------------------------------------------
#$Date: 2020-02-04 04:15:36 +0100 (mar 04 de feb de 2020) $
#$Revision: 247535 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/39/4133916.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4133916
loop_
_publ_author_name
'Jin, Shengfei'
'Dang, Hang T.'
'Haug, Graham C.'
'He, Ru'
'Nguyen, Viet D.'
'Nguyen, Vu T.'
'Arman, Hadi D.'
'Schanze, Kirk S.'
'Larionov, Oleg V.'
_publ_section_title
;
 Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1603
_journal_page_last               1613
_journal_paper_doi               10.1021/jacs.9b12519
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C6 H7 B F3 N, H2 O'
_chemical_formula_sum            'C6 H9 B F3 N O'
_chemical_formula_weight         178.95
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.676(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5748(2)
_cell_length_b                   7.5235(2)
_cell_length_c                   13.5891(4)
_cell_measurement_reflns_used    6253
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.0660
_cell_measurement_theta_min      2.9860
_cell_volume                     774.10(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -97.00  82.00   1.00    5.00    --   -7.70  -7.00  56.00  179
  2  ω    -21.00  94.00   1.00    5.00    --    4.20  38.00-180.00  115
  3  ω    -97.00  23.00   1.00    5.00    --   -7.70 -57.00-120.00  120
  4  ω    -41.00  82.00   1.00    5.00    --   -7.70  72.00  60.00  123
  5  ω    -41.00 -16.00   1.00    5.00    --   -7.70  72.00 -60.00   25
  6  ω    -33.00  82.00   1.00    5.00    --   -7.70  38.00-150.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0207007000
_diffrn_orient_matrix_UB_12      -0.0065176000
_diffrn_orient_matrix_UB_13      0.0511329000
_diffrn_orient_matrix_UB_21      -0.0911347000
_diffrn_orient_matrix_UB_22      0.0048413000
_diffrn_orient_matrix_UB_23      0.0102213000
_diffrn_orient_matrix_UB_31      -0.0061827000
_diffrn_orient_matrix_UB_32      -0.0939239000
_diffrn_orient_matrix_UB_33      -0.0030341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15109
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.486
_diffrn_reflns_theta_min         2.690
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       plank
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0343
_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/[σ²(Fo²)+(0.0400P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1590
_reflns_number_total             1606
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cd1870.cif
_cod_data_source_block           cd1870
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133916
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C6H6B1F3K1N1
_chemical_oxdiff_usercomment     HDA488-16
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All B(H,H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A), C2(H2)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.087
_oxdiff_exptl_absorpt_empirical_full_min 0.926
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F2 F 0.86751(10) 0.70000(10) 0.72104(6) 0.0211(2) Uani 1 1 d .
F1 F 0.67933(10) 0.46409(11) 0.72849(6) 0.0220(2) Uani 1 1 d .
F3 F 0.90774(10) 0.45811(11) 0.62236(6) 0.0224(2) Uani 1 1 d .
O1 O 0.20151(13) 0.93672(14) 0.29620(8) 0.0238(2) Uani 1 1 d .
N1 N 0.42360(14) 0.80502(14) 0.43999(8) 0.0155(2) Uani 1 1 d .
C3 C 0.65081(16) 0.65679(16) 0.57992(9) 0.0145(3) Uani 1 1 d .
C4 C 0.47862(16) 0.70546(16) 0.60169(9) 0.0151(3) Uani 1 1 d .
H4 H 0.438672 0.687663 0.666573 0.018 Uiso 1 1 calc R
C1 C 0.58933(17) 0.76177(18) 0.41486(9) 0.0176(3) Uani 1 1 d .
H1A H 0.626390 0.782580 0.349672 0.021 Uiso 1 1 calc R
C5 C 0.36403(16) 0.77902(16) 0.53147(9) 0.0151(3) Uani 1 1 d .
C2 C 0.70443(16) 0.68782(17) 0.48320(9) 0.0164(3) Uani 1 1 d .
H2 H 0.820805 0.657485 0.465086 0.020 Uiso 1 1 calc R
C6 C 0.17663(17) 0.82636(18) 0.55051(10) 0.0199(3) Uani 1 1 d .
H6A H 0.124965 0.887678 0.492928 0.030 Uiso 1 1 calc GR
H6B H 0.172613 0.904610 0.608056 0.030 Uiso 1 1 calc GR
H6C H 0.109331 0.717848 0.563045 0.030 Uiso 1 1 calc GR
B1 B 0.77859(18) 0.56493(19) 0.66359(10) 0.0157(3) Uani 1 1 d .
H1 H 0.347(2) 0.851(2) 0.3922(12) 0.019 Uiso 1 1 d R
H1B H 0.175(2) 1.042(3) 0.2886(13) 0.023 Uiso 1 1 d R
H1C H 0.113(2) 0.876(2) 0.2774(12) 0.023 Uiso 1 1 d R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F2 0.0206(4) 0.0179(4) 0.0240(4) -0.0032(3) -0.0092(3) 0.0010(3)
F1 0.0236(4) 0.0232(4) 0.0190(4) 0.0058(3) -0.0025(3) -0.0018(3)
F3 0.0209(4) 0.0229(4) 0.0232(4) -0.0035(3) -0.0021(3) 0.0084(3)
O1 0.0223(5) 0.0168(5) 0.0314(6) 0.0025(4) -0.0126(4) -0.0010(4)
N1 0.0154(5) 0.0151(5) 0.0157(5) 0.0017(4) -0.0042(4) -0.0006(4)
C3 0.0151(6) 0.0120(6) 0.0161(6) -0.0016(4) -0.0027(5) -0.0017(4)
C4 0.0161(6) 0.0154(6) 0.0138(6) -0.0012(4) 0.0000(4) -0.0008(5)
C1 0.0176(6) 0.0201(6) 0.0151(6) 0.0010(5) 0.0003(5) -0.0029(5)
C5 0.0149(6) 0.0129(6) 0.0175(6) -0.0022(5) -0.0018(5) -0.0017(5)
C2 0.0130(6) 0.0183(6) 0.0180(6) -0.0002(5) 0.0006(5) -0.0015(5)
C6 0.0146(6) 0.0238(7) 0.0211(6) -0.0023(5) -0.0021(5) 0.0032(5)
B1 0.0159(6) 0.0150(7) 0.0159(7) -0.0010(5) -0.0028(5) 0.0012(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1B O1 H1C 106.6(17)
C1 N1 H1 118.7(10)
C5 N1 C1 122.45(11)
C5 N1 H1 118.8(10)
C4 C3 C2 116.87(11)
C4 C3 B1 120.30(11)
C2 C3 B1 122.81(11)
C3 C4 H4 119.0
C5 C4 C3 121.97(11)
C5 C4 H4 119.0
N1 C1 H1A 119.9
N1 C1 C2 120.21(12)
C2 C1 H1A 119.9
N1 C5 C4 118.20(11)
N1 C5 C6 118.05(11)
C4 C5 C6 123.72(11)
C3 C2 H2 119.9
C1 C2 C3 120.29(12)
C1 C2 H2 119.9
C5 C6 H6A 109.5
C5 C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6B 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
F2 B1 C3 109.84(10)
F1 B1 F2 107.04(10)
F1 B1 C3 110.58(10)
F3 B1 F2 107.60(10)
F3 B1 F1 109.67(11)
F3 B1 C3 111.96(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F2 B1 1.4370(16)
F1 B1 1.3991(16)
F3 B1 1.3960(16)
O1 H1B 0.826(19)
O1 H1C 0.845(19)
N1 C1 1.3504(17)
N1 C5 1.3491(17)
N1 H1 0.924(16)
C3 C4 1.3948(17)
C3 C2 1.4065(17)
C3 B1 1.6257(18)
C4 H4 0.9500
C4 C5 1.3862(17)
C1 H1A 0.9500
C1 C2 1.3729(18)
C5 C6 1.4935(17)
C2 H2 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
