#------------------------------------------------------------------------------
#$Date: 2017-08-05 21:55:14 +0300 (Sat, 05 Aug 2017) $
#$Revision: 199595 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/65/1546546.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_1546546
loop_
_publ_author_name
'Raju, Selvam'
'Annamalai, Pratheepkumar'
'Chen, Pei-Ling'
'Liu, Yi-Hung'
'Chuang, Shih-Ching'
_publ_section_title
;
 Palladium-Catalyzed C-H Bond Activation by Using Iminoquinone as a
 Directing Group and an Internal Oxidant or a Co-oxidant: Production of
 Dihydrophenanthridines, Phenanthridines, and Carbazoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4134
_journal_page_last               4137
_journal_paper_doi               10.1021/acs.orglett.7b01956
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C19 H12 F3 N O2'
_chemical_formula_weight         343.30
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.621(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1959(4)
_cell_length_b                   6.6152(2)
_cell_length_c                   19.9552(7)
_cell_measurement_reflns_used    1321
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      73.4860
_cell_measurement_theta_min      4.2830
_cell_volume                     1609.31(9)
_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    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5482
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.973
_diffrn_reflns_theta_min         4.196
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85684
_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_density_diffrn    1.417
_exptl_crystal_description       column
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1721
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1856
_reflns_number_total             2920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b01956_si_002.cif
_cod_data_source_block           ic17746
_cod_depositor_comments
'Adding full bibliography for 1546544--1546547.cif.'
_cod_database_code               1546546
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
F1 F 0.2781(2) 0.9867(5) 0.28123(15) 0.0939(9) Uani 1 1 d . .
F2 F 0.3275(3) 0.9827(7) 0.18081(14) 0.1250(16) Uani 1 1 d . .
F3 F 0.4103(2) 1.1725(4) 0.2510(2) 0.1034(10) Uani 1 1 d . .
O1 O 0.43110(18) 0.8418(4) 0.25958(11) 0.0524(6) Uani 1 1 d . .
O2 O 1.1130(2) 1.3275(4) 0.06524(14) 0.0630(7) Uani 1 1 d . .
N1 N 0.82506(18) 0.7454(3) 0.12696(11) 0.0328(5) Uani 1 1 d . .
C1 C 0.7224(2) 0.7823(4) 0.15588(13) 0.0324(6) Uani 1 1 d . .
C2 C 0.7157(2) 0.9142(4) 0.21056(13) 0.0374(6) Uani 1 1 d . .
H2A H 0.7786 0.9895 0.2245 0.045 Uiso 1 1 calc R U
C3 C 0.6192(3) 0.9371(4) 0.24476(14) 0.0415(7) Uani 1 1 d . .
H3A H 0.6154 1.0270 0.2817 0.050 Uiso 1 1 calc R U
C4 C 0.5289(2) 0.8259(5) 0.22378(14) 0.0401(6) Uani 1 1 d . .
C5 C 0.5331(2) 0.6904(4) 0.17159(14) 0.0375(6) Uani 1 1 d . .
H5A H 0.4698 0.6143 0.1590 0.045 Uiso 1 1 calc R U
C6 C 0.6300(2) 0.6642(4) 0.13701(13) 0.0325(6) Uani 1 1 d . .
C7 C 0.6338(2) 0.5083(4) 0.08378(13) 0.0322(6) Uani 1 1 d . .
C8 C 0.5831(2) 0.3207(4) 0.09361(14) 0.0370(6) Uani 1 1 d . .
H8A H 0.5472 0.2955 0.1344 0.044 Uiso 1 1 calc R U
C9 C 0.5842(2) 0.1724(5) 0.04521(15) 0.0416(7) Uani 1 1 d . .
H9A H 0.5503 0.0457 0.0531 0.050 Uiso 1 1 calc R U
C10 C 0.6351(2) 0.2084(5) -0.01540(15) 0.0446(7) Uani 1 1 d . .
H10A H 0.6357 0.1068 -0.0490 0.054 Uiso 1 1 calc R U
C11 C 0.6846(2) 0.3925(5) -0.02607(14) 0.0437(7) Uani 1 1 d . .
H11A H 0.7194 0.4174 -0.0673 0.052 Uiso 1 1 calc R U
C12 C 0.6840(2) 0.5417(4) 0.02266(14) 0.0377(6) Uani 1 1 d . .
H12A H 0.7181 0.6681 0.0144 0.045 Uiso 1 1 calc R U
C13 C 0.8889(2) 0.8919(4) 0.10989(13) 0.0316(6) Uani 1 1 d . .
C14 C 1.0019(2) 0.8387(4) 0.09297(14) 0.0371(6) Uani 1 1 d . .
H14A H 1.0231 0.7005 0.0919 0.045 Uiso 1 1 calc R U
C15 C 1.0752(2) 0.9815(5) 0.07903(16) 0.0433(7) Uani 1 1 d . .
H15A H 1.1483 0.9429 0.0701 0.052 Uiso 1 1 calc R U
C16 C 1.0458(2) 1.1966(5) 0.07718(15) 0.0421(7) Uani 1 1 d . .
C17 C 0.9304(2) 1.2462(4) 0.08903(14) 0.0396(6) Uani 1 1 d . .
H17A H 0.9071 1.3828 0.0853 0.047 Uiso 1 1 calc R U
C18 C 0.8578(2) 1.1052(4) 0.10484(13) 0.0344(6) Uani 1 1 d . .
H18A H 0.7844 1.1437 0.1130 0.041 Uiso 1 1 calc R U
C19 C 0.3636(3) 0.9936(7) 0.24232(19) 0.0619(10) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C19 O1 C4 116.7(3)
C13 N1 C1 121.6(2)
C2 C1 N1 119.8(2)
C2 C1 C6 119.2(3)
N1 C1 C6 120.3(2)
C3 C2 C1 121.4(3)
C4 C3 C2 118.3(3)
C3 C4 C5 122.0(3)
C3 C4 O1 119.1(3)
C5 C4 O1 118.8(3)
C4 C5 C6 120.4(3)
C5 C6 C1 118.6(3)
C5 C6 C7 119.0(2)
C1 C6 C7 122.3(2)
C12 C7 C8 117.9(3)
C12 C7 C6 122.6(2)
C8 C7 C6 119.5(2)
C9 C8 C7 121.3(3)
C8 C9 C10 120.0(3)
C11 C10 C9 119.5(3)
C10 C11 C12 120.7(3)
C11 C12 C7 120.7(3)
N1 C13 C18 125.7(3)
N1 C13 C14 117.1(2)
C18 C13 C14 117.2(2)
C15 C14 C13 121.0(3)
C14 C15 C16 121.8(3)
O2 C16 C15 121.8(3)
O2 C16 C17 121.6(3)
C15 C16 C17 116.5(3)
C18 C17 C16 121.9(3)
C17 C18 C13 121.3(3)
F2 C19 F1 107.7(3)
F2 C19 O1 113.1(3)
F1 C19 O1 108.3(4)
F2 C19 F3 107.9(4)
F1 C19 F3 107.4(3)
O1 C19 F3 112.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C19 1.318(4)
F2 C19 1.294(5)
F3 C19 1.323(5)
O1 C19 1.337(5)
O1 C4 1.411(4)
O2 C16 1.221(4)
N1 C13 1.295(4)
N1 C1 1.415(4)
C1 C2 1.401(4)
C1 C6 1.413(4)
C2 C3 1.385(4)
C3 C4 1.380(4)
C4 C5 1.376(4)
C5 C6 1.396(4)
C6 C7 1.482(4)
C7 C12 1.398(4)
C7 C8 1.403(4)
C8 C9 1.377(4)
C9 C10 1.396(5)
C10 C11 1.378(5)
C11 C12 1.386(4)
C13 C18 1.463(4)
C13 C14 1.472(4)
C14 C15 1.335(4)
C15 C16 1.467(5)
C16 C17 1.470(4)
C17 C18 1.330(4)
