#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:23:07 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038055.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_4038055
loop_
_publ_author_name
'Jia, Chunqi'
'Wu, Nini'
'Cai, Xiaofeng'
'Li, Gang'
'Zhong, Lei'
'Zou, Lei'
'Cui, Xiuling'
_publ_section_title
;
 Ruthenium-Catalyzed meta-Selective CAr-H Bond
 Formylation of Arenes.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4536
_journal_page_last               4542
_journal_paper_doi               10.1021/acs.joc.0c00007
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C18 H14 F0 N2 O0'
_chemical_formula_weight         258.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.003(3)
_cell_length_b                   7.6071(15)
_cell_length_c                   11.779(2)
_cell_measurement_reflns_used    2430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.69
_cell_volume                     1357.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11459
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0810
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0811P)²+2.1686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2426
_refine_ls_wR_factor_ref         0.2565
_reflns_number_gt                2228
_reflns_number_total             3351
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo0c00007_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038055.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4038055
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.2591(2) 0.5329(4) 0.2660(3) 0.0398(7) Uani 1 1 d . . .
C11 C 0.36434(19) 0.6282(4) 0.4560(3) 0.0368(6) Uani 1 1 d . . .
C10 C 0.33914(19) 0.6138(4) 0.3311(3) 0.0382(7) Uani 1 1 d . . .
H10A H 0.3758 0.6583 0.2906 0.046 Uiso 1 1 calc R . .
C6 C 0.1301(2) 0.4661(4) -0.0718(3) 0.0414(7) Uani 1 1 d . . .
C12 C 0.3100(2) 0.5597(4) 0.5160(3) 0.0432(7) Uani 1 1 d . . .
H12A H 0.3259 0.5701 0.5989 0.052 Uiso 1 1 calc R . .
C15 C 0.44963(19) 0.7143(4) 0.5236(2) 0.0362(6) Uani 1 1 d . . .
C7 C 0.1577(2) 0.4689(5) 0.0600(3) 0.0459(8) Uani 1 1 d . . .
H7A H 0.1176 0.4246 0.0951 0.055 Uiso 1 1 calc R . .
N1 N 0.45914(18) 0.7579(4) 0.6372(2) 0.0512(8) Uani 1 1 d . . .
N2 N 0.50806(17) 0.7408(4) 0.4675(2) 0.0438(6) Uani 1 1 d . . .
C8 C 0.2339(2) 0.5281(5) 0.1341(3) 0.0447(8) Uani 1 1 d . . .
H8A H 0.2748 0.5701 0.0998 0.054 Uiso 1 1 calc R . .
C1 C 0.0507(2) 0.3818(5) -0.1351(3) 0.0505(8) Uani 1 1 d . . .
H1A H 0.0165 0.3313 -0.0932 0.061 Uiso 1 1 calc R . .
C14 C 0.2073(2) 0.4627(5) 0.3294(3) 0.0474(8) Uani 1 1 d . . .
H14A H 0.1549 0.4058 0.2880 0.057 Uiso 1 1 calc R . .
C13 C 0.2322(2) 0.4759(5) 0.4528(3) 0.0486(8) Uani 1 1 d . . .
H13A H 0.1965 0.4282 0.4936 0.058 Uiso 1 1 calc R . .
C5 C 0.1777(2) 0.5435(5) -0.1384(3) 0.0472(8) Uani 1 1 d . . .
H5A H 0.2299 0.6023 -0.0987 0.057 Uiso 1 1 calc R . .
C3 C 0.0716(3) 0.4492(5) -0.3223(3) 0.0595(10) Uani 1 1 d . . .
H3A H 0.0525 0.4431 -0.4056 0.071 Uiso 1 1 calc R . .
C4 C 0.1496(2) 0.5353(5) -0.2616(3) 0.0540(9) Uani 1 1 d . . .
H4A H 0.1829 0.5874 -0.3042 0.065 Uiso 1 1 calc R . .
C2 C 0.0226(2) 0.3730(5) -0.2591(3) 0.0562(10) Uani 1 1 d . . .
H2A H -0.0298 0.3151 -0.2997 0.067 Uiso 1 1 calc R . .
C16 C 0.5835(2) 0.8175(5) 0.5306(3) 0.0487(8) Uani 1 1 d . . .
H16A H 0.6258 0.8394 0.4937 0.058 Uiso 1 1 calc R . .
C17 C 0.6009(2) 0.8652(5) 0.6481(3) 0.0528(9) Uani 1 1 d . . .
H17A H 0.6543 0.9165 0.6918 0.063 Uiso 1 1 calc R . .
C18 C 0.5359(3) 0.8340(6) 0.6986(3) 0.0609(10) Uani 1 1 d . . .
H18A H 0.5455 0.8668 0.7778 0.073 Uiso 1 1 calc R . .
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'
N N 0.0061 0.0033 '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'
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
C14 C9 C10 118.2(3) . . ?
C14 C9 C8 123.3(3) . . ?
C10 C9 C8 118.5(3) . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 C15 120.6(3) . . ?
C10 C11 C15 120.0(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 123.9(3) . . ?
C1 C6 C7 118.6(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
N2 C15 N1 126.2(3) . . ?
N2 C15 C11 118.2(3) . . ?
N1 C15 C11 115.6(3) . . ?
C8 C7 C6 126.7(3) . . ?
C8 C7 H7A 116.7 . . ?
C6 C7 H7A 116.7 . . ?
C15 N1 C18 115.8(3) . . ?
C16 N2 C15 116.6(3) . . ?
C7 C8 C9 125.6(3) . . ?
C7 C8 H8A 117.2 . . ?
C9 C8 H8A 117.2 . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14A 119.4 . . ?
C9 C14 H14A 119.4 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
N2 C16 C17 122.1(3) . . ?
N2 C16 H16A 118.9 . . ?
C17 C16 H16A 118.9 . . ?
C18 C17 C16 117.1(3) . . ?
C18 C17 H17A 121.4 . . ?
C16 C17 H17A 121.4 . . ?
N1 C18 C17 122.1(3) . . ?
N1 C18 H18A 119.0 . . ?
C17 C18 H18A 119.0 . . ?
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
C9 C14 1.389(4) . ?
C9 C10 1.405(4) . ?
C9 C8 1.474(4) . ?
C11 C12 1.388(4) . ?
C11 C10 1.398(4) . ?
C11 C15 1.492(4) . ?
C10 H10A 0.9300 . ?
C6 C5 1.389(5) . ?
C6 C1 1.404(4) . ?
C6 C7 1.471(4) . ?
C12 C13 1.383(5) . ?
C12 H12A 0.9300 . ?
C15 N2 1.323(4) . ?
C15 N1 1.338(4) . ?
C7 C8 1.329(4) . ?
C7 H7A 0.9300 . ?
N1 C18 1.340(4) . ?
N2 C16 1.331(4) . ?
C8 H8A 0.9300 . ?
C1 C2 1.384(5) . ?
C1 H1A 0.9300 . ?
C14 C13 1.382(4) . ?
C14 H14A 0.9300 . ?
C13 H13A 0.9300 . ?
C5 C4 1.375(4) . ?
C5 H5A 0.9300 . ?
C3 C2 1.371(6) . ?
C3 C4 1.387(5) . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C2 H2A 0.9300 . ?
C16 C17 1.370(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.375(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C11 C10 C9 0.8(5) . . . . ?
C15 C11 C10 C9 179.9(3) . . . . ?
C14 C9 C10 C11 -2.1(5) . . . . ?
C8 C9 C10 C11 177.4(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C15 C11 C12 C13 -178.3(3) . . . . ?
C12 C11 C15 N2 164.7(3) . . . . ?
C10 C11 C15 N2 -14.5(4) . . . . ?
C12 C11 C15 N1 -15.4(4) . . . . ?
C10 C11 C15 N1 165.4(3) . . . . ?
C5 C6 C7 C8 -7.0(6) . . . . ?
C1 C6 C7 C8 173.5(4) . . . . ?
N2 C15 N1 C18 -0.6(5) . . . . ?
C11 C15 N1 C18 179.5(3) . . . . ?
N1 C15 N2 C16 0.3(5) . . . . ?
C11 C15 N2 C16 -179.8(3) . . . . ?
C6 C7 C8 C9 178.6(3) . . . . ?
C14 C9 C8 C7 4.9(5) . . . . ?
C10 C9 C8 C7 -174.5(3) . . . . ?
C5 C6 C1 C2 1.6(5) . . . . ?
C7 C6 C1 C2 -178.9(3) . . . . ?
C10 C9 C14 C13 1.8(5) . . . . ?
C8 C9 C14 C13 -177.7(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C9 C14 C13 C12 -0.1(5) . . . . ?
C1 C6 C5 C4 -1.4(5) . . . . ?
C7 C6 C5 C4 179.2(3) . . . . ?
C6 C5 C4 C3 0.5(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C15 N2 C16 C17 0.7(5) . . . . ?
N2 C16 C17 C18 -1.4(6) . . . . ?
C15 N1 C18 C17 -0.1(6) . . . . ?
C16 C17 C18 N1 1.0(6) . . . . ?
