#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:54:09 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038510.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_4038510
loop_
_publ_author_name
'Wang, Dandan'
'Guo, Xing'
'Wu, Hao'
'Wu, Qinghua'
'Wang, Hua'
'Zhang, Xiankang'
'Hao, Erhong'
'Jiao, Lijuan'
_publ_section_title
;
 Visible Light Excitation of BODIPYs Enables Dehydrogenative Enamination
 at Their α-Positions with Aliphatic Amines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8360
_journal_page_last               8370
_journal_paper_doi               10.1021/acs.joc.0c00620
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C21 H17 B F7 N3'
_chemical_formula_sum            'C21 H17 B F7 N3'
_chemical_formula_weight         455.19
_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
_audit_creation_date             2018-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.785(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1713(7)
_cell_length_b                   13.6990(5)
_cell_length_c                   8.3562(3)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.96
_cell_volume                     2060.93(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            76057
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.875
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1107 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.9205.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0652
_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)+(0.0932P)²+1.3521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3237
_reflns_number_total             4725
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00620_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 4038510--4038515.cif.'
_cod_database_code               4038510
_shelx_shelxl_version_number     2014/7
_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.
;
_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 Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00V(H00K,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N),
 C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00U(H00C,H00D,H00G), C00W(H00L,H00O,H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.87595(9) 0.47714(12) 0.7127(3) 0.0847(6) Uani 1 1 d . . . . .
F002 F 0.68623(10) 0.51976(16) 0.1262(2) 0.0820(5) Uani 1 1 d . . . . .
F003 F 0.78854(13) 0.46089(13) 0.87689(19) 0.0861(6) Uani 1 1 d . . . . .
F004 F 0.53602(11) 0.60284(17) 0.5215(2) 0.0885(6) Uani 1 1 d . . . . .
N005 N 0.75747(10) 0.41071(13) 0.6010(2) 0.0457(4) Uani 1 1 d . . . . .
F006 F 0.58000(14) 0.58421(18) -0.1037(2) 0.1017(7) Uani 1 1 d . . . . .
F007 F 0.42849(11) 0.66049(19) 0.2897(3) 0.1097(8) Uani 1 1 d . . . . .
N008 N 0.77156(11) 0.58493(14) 0.6738(3) 0.0528(5) Uani 1 1 d . . . . .
F009 F 0.45031(13) 0.65385(16) -0.0231(3) 0.1075(8) Uani 1 1 d . . . . .
N00A N 0.87861(13) 0.10751(16) 0.7782(3) 0.0636(6) Uani 1 1 d . . . . .
C00B C 0.61527(13) 0.55964(17) 0.3317(3) 0.0508(5) Uani 1 1 d . . . . .
C00C C 0.76605(12) 0.31205(16) 0.5976(3) 0.0449(5) Uani 1 1 d . . . . .
C00D C 0.67650(13) 0.53168(17) 0.4601(3) 0.0481(5) Uani 1 1 d . . . . .
C00E C 0.66841(13) 0.34835(17) 0.4100(3) 0.0519(6) Uani 1 1 d . . . . .
H00E H 0.6282 0.3437 0.3287 0.062 Uiso 1 1 calc R . . . .
C00F C 0.70915(13) 0.27346(17) 0.4770(3) 0.0513(5) Uani 1 1 d . . . . .
H00F H 0.7019 0.2079 0.4502 0.062 Uiso 1 1 calc R . . . .
C00G C 0.69750(12) 0.43647(17) 0.4854(3) 0.0463(5) Uani 1 1 d . . . . .
C00H C 0.82280(13) 0.26293(17) 0.6958(3) 0.0499(5) Uani 1 1 d . . . . .
H00H H 0.8571 0.2985 0.7654 0.060 Uiso 1 1 calc R . . . .
C00I C 0.71437(14) 0.60762(17) 0.5530(3) 0.0511(5) Uani 1 1 d . . . . .
C00J C 0.82864(14) 0.16320(18) 0.6908(3) 0.0544(6) Uani 1 1 d . . . . .
H00J H 0.7936 0.1310 0.6180 0.065 Uiso 1 1 calc R . . . .
C00K C 0.62337(14) 0.55494(19) 0.1702(3) 0.0570(6) Uani 1 1 d . . . . .
C00L C 0.54841(16) 0.5965(2) 0.3683(3) 0.0620(7) Uani 1 1 d . . . . .
C00M C 0.70681(17) 0.70836(19) 0.5455(4) 0.0646(7) Uani 1 1 d . . . . .
H00M H 0.6726 0.7433 0.4749 0.078 Uiso 1 1 calc R . . . .
C00N C 0.79862(17) 0.6708(2) 0.7401(4) 0.0684(7) Uani 1 1 d . . . . .
H00N H 0.8374 0.6765 0.8244 0.082 Uiso 1 1 calc R . . . .
C00O C 0.49322(16) 0.6278(2) 0.2502(4) 0.0717(8) Uani 1 1 d . . . . .
C00P C 0.56901(18) 0.5884(2) 0.0514(3) 0.0668(7) Uani 1 1 d . . . . .
C00Q C 0.93689(16) 0.1494(2) 0.8956(4) 0.0700(8) Uani 1 1 d . . . . .
H00A H 0.9543 0.1001 0.9751 0.084 Uiso 1 1 calc R . . . .
H00B H 0.9162 0.2027 0.9515 0.084 Uiso 1 1 calc R . . . .
C00R C 0.76021(19) 0.7473(2) 0.6639(4) 0.0766(8) Uani 1 1 d . . . . .
H00R H 0.7682 0.8132 0.6868 0.092 Uiso 1 1 calc R . . . .
C00S C 0.50372(18) 0.6240(2) 0.0933(4) 0.0709(8) Uani 1 1 d . . . . .
B00T B 0.80016(16) 0.4833(2) 0.7208(3) 0.0528(6) Uani 1 1 d . . . . .
C00U C 1.0012(2) 0.1863(3) 0.8196(6) 0.1054(13) Uani 1 1 d . . . . .
H00C H 0.9855 0.2402 0.7497 0.158 Uiso 1 1 calc GR . . . .
H00D H 1.0198 0.1350 0.7578 0.158 Uiso 1 1 calc GR . . . .
H00G H 1.0398 0.2075 0.9023 0.158 Uiso 1 1 calc GR . . . .
C00V C 0.8742(2) 0.0009(2) 0.7620(6) 0.1003(13) Uani 1 1 d . . . . .
H00K H 0.8784 -0.0274 0.8693 0.120 Uiso 1 1 calc R . . . .
H00I H 0.8255 -0.0159 0.7064 0.120 Uiso 1 1 calc R . . . .
C00W C 0.9287(3) -0.0423(3) 0.6782(7) 0.1226(17) Uani 1 1 d . . . . .
H00L H 0.9241 -0.0167 0.5703 0.184 Uiso 1 1 calc GR . . . .
H00O H 0.9216 -0.1117 0.6740 0.184 Uiso 1 1 calc GR . . . .
H00P H 0.9773 -0.0277 0.7334 0.184 Uiso 1 1 calc GR . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C N005 C00G 108.43(18) . . ?
C00C N005 B00T 127.18(19) . . ?
C00G N005 B00T 124.14(19) . . ?
C00I N008 B00T 126.30(19) . . ?
C00N N008 C00I 107.3(2) . . ?
C00N N008 B00T 126.4(2) . . ?
C00J N00A C00Q 121.6(2) . . ?
C00J N00A C00V 119.8(3) . . ?
C00Q N00A C00V 118.6(2) . . ?
C00K C00B C00D 121.7(2) . . ?
C00K C00B C00L 116.5(2) . . ?
C00L C00B C00D 121.8(2) . . ?
N005 C00C C00F 107.78(19) . . ?
N005 C00C C00H 122.8(2) . . ?
C00H C00C C00F 129.4(2) . . ?
C00G C00D C00B 121.5(2) . . ?
C00G C00D C00I 120.7(2) . . ?
C00I C00D C00B 117.8(2) . . ?
C00F C00E H00E 125.9 . . ?
C00F C00E C00G 108.2(2) . . ?
C00G C00E H00E 125.9 . . ?
C00C C00F H00F 125.9 . . ?
C00E C00F C00C 108.3(2) . . ?
C00E C00F H00F 125.9 . . ?
N005 C00G C00E 107.34(19) . . ?
C00D C00G N005 121.5(2) . . ?
C00D C00G C00E 131.2(2) . . ?
C00C C00H H00H 119.5 . . ?
C00J C00H C00C 121.0(2) . . ?
C00J C00H H00H 119.5 . . ?
N008 C00I C00D 119.7(2) . . ?
N008 C00I C00M 108.4(2) . . ?
C00M C00I C00D 131.8(2) . . ?
N00A C00J C00H 127.3(2) . . ?
N00A C00J H00J 116.3 . . ?
C00H C00J H00J 116.3 . . ?
F002 C00K C00B 119.6(2) . . ?
F002 C00K C00P 118.5(2) . . ?
C00B C00K C00P 121.9(3) . . ?
F004 C00L C00B 120.2(2) . . ?
F004 C00L C00O 117.8(3) . . ?
C00O C00L C00B 122.0(3) . . ?
C00I C00M H00M 126.4 . . ?
C00I C00M C00R 107.1(3) . . ?
C00R C00M H00M 126.4 . . ?
N008 C00N H00N 125.1 . . ?
N008 C00N C00R 109.8(3) . . ?
C00R C00N H00N 125.1 . . ?
F007 C00O C00L 120.4(3) . . ?
F007 C00O C00S 119.7(3) . . ?
C00S C00O C00L 119.9(3) . . ?
F006 C00P C00K 119.7(3) . . ?
F006 C00P C00S 120.7(3) . . ?
C00S C00P C00K 119.6(3) . . ?
N00A C00Q H00A 109.1 . . ?
N00A C00Q H00B 109.1 . . ?
N00A C00Q C00U 112.7(3) . . ?
H00A C00Q H00B 107.8 . . ?
C00U C00Q H00A 109.1 . . ?
C00U C00Q H00B 109.1 . . ?
C00M C00R H00R 126.3 . . ?
C00N C00R C00M 107.4(2) . . ?
C00N C00R H00R 126.3 . . ?
F009 C00S C00O 120.5(3) . . ?
F009 C00S C00P 119.3(3) . . ?
C00O C00S C00P 120.2(3) . . ?
F001 B00T N005 110.1(2) . . ?
F001 B00T N008 110.4(2) . . ?
F003 B00T F001 108.1(2) . . ?
F003 B00T N005 109.9(2) . . ?
F003 B00T N008 110.9(2) . . ?
N008 B00T N005 107.35(19) . . ?
C00Q C00U H00C 109.5 . . ?
C00Q C00U H00D 109.5 . . ?
C00Q C00U H00G 109.5 . . ?
H00C C00U H00D 109.5 . . ?
H00C C00U H00G 109.5 . . ?
H00D C00U H00G 109.5 . . ?
N00A C00V H00K 108.4 . . ?
N00A C00V H00I 108.4 . . ?
H00K C00V H00I 107.5 . . ?
C00W C00V N00A 115.3(4) . . ?
C00W C00V H00K 108.4 . . ?
C00W C00V H00I 108.4 . . ?
C00V C00W H00L 109.5 . . ?
C00V C00W H00O 109.5 . . ?
C00V C00W H00P 109.5 . . ?
H00L C00W H00O 109.5 . . ?
H00L C00W H00P 109.5 . . ?
H00O C00W H00P 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 B00T 1.390(3) . ?
F002 C00K 1.336(3) . ?
F003 B00T 1.383(3) . ?
F004 C00L 1.333(3) . ?
N005 C00C 1.361(3) . ?
N005 C00G 1.400(3) . ?
N005 B00T 1.543(3) . ?
F006 C00P 1.339(3) . ?
F007 C00O 1.341(3) . ?
N008 C00I 1.383(3) . ?
N008 C00N 1.363(3) . ?
N008 B00T 1.519(3) . ?
F009 C00S 1.342(3) . ?
N00A C00J 1.327(3) . ?
N00A C00Q 1.460(4) . ?
N00A C00V 1.467(4) . ?
C00B C00D 1.487(3) . ?
C00B C00K 1.378(4) . ?
C00B C00L 1.388(4) . ?
C00C C00F 1.443(3) . ?
C00C C00H 1.400(3) . ?
C00D C00G 1.367(3) . ?
C00D C00I 1.419(3) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.342(3) . ?
C00E C00G 1.429(3) . ?
C00F H00F 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00J 1.371(3) . ?
C00I C00M 1.387(3) . ?
C00J H00J 0.9300 . ?
C00K C00P 1.381(4) . ?
C00L C00O 1.377(4) . ?
C00M H00M 0.9300 . ?
C00M C00R 1.395(4) . ?
C00N H00N 0.9300 . ?
C00N C00R 1.368(4) . ?
C00O C00S 1.351(5) . ?
C00P C00S 1.371(5) . ?
C00Q H00A 0.9700 . ?
C00Q H00B 0.9700 . ?
C00Q C00U 1.492(5) . ?
C00R H00R 0.9300 . ?
C00U H00C 0.9600 . ?
C00U H00D 0.9600 . ?
C00U H00G 0.9600 . ?
C00V H00K 0.9700 . ?
C00V H00I 0.9700 . ?
C00V C00W 1.418(7) . ?
C00W H00L 0.9600 . ?
C00W H00O 0.9600 . ?
C00W H00P 0.9600 . ?
