#------------------------------------------------------------------------------
#$Date: 2019-11-25 15:32:12 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/08/4130851.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_4130851
loop_
_publ_author_name
'Xie, Weilong'
'Yoon, Jung Hee'
'Chang, Sukbok'
_publ_section_title
;
 (NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable
 Carbamates: Scope and Mechanistic Studies.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12605
_journal_page_last               12614
_journal_paper_doi               10.1021/jacs.6b07486
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C33 H30 Cu F5 N2'
_chemical_formula_weight         613.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 99.651(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4885(5)
_cell_length_b                   22.9762(15)
_cell_length_c                   15.9265(10)
_cell_measurement_reflns_used    7213
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.916
_cell_measurement_theta_min      3.075
_cell_volume                     3062.2(3)
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_collection       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1258
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38779
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         3.075
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_correction_T_min  0.8254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.899
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1145P)²+16.8222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1956
_refine_ls_wR_factor_ref         0.2198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2638
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b07486_si_002.cif
_cod_data_source_block           c2c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4130851
_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_min   0.825
_shelx_estimated_absorpt_t_max   0.941
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5000 0.50426(3) 0.7500 0.0250(3) Uani 1 2 d S T P
C1 C 0.5000 0.4221(2) 0.7500 0.0243(11) Uani 1 2 d S T P
C2 C 0.5365(7) 0.32777(19) 0.7911(3) 0.0398(11) Uani 1 1 d . . .
H2 H 0.5663 0.2946 0.8258 0.048 Uiso 1 1 calc R U .
C3 C 0.6384(5) 0.40506(17) 0.8970(2) 0.0265(9) Uani 1 1 d . . .
C4 C 0.8031(5) 0.41222(19) 0.9099(3) 0.0312(9) Uani 1 1 d . . .
C5 C 0.8982(7) 0.3988(3) 0.8399(3) 0.0444(12) Uani 1 1 d . . .
H5A H 0.8786 0.3584 0.8212 0.067 Uiso 1 1 calc R U .
H5B H 1.0123 0.4042 0.8615 0.067 Uiso 1 1 calc R U .
H5C H 0.8652 0.4251 0.7917 0.067 Uiso 1 1 calc R U .
C6 C 0.8780(5) 0.4310(2) 0.9899(3) 0.0321(9) Uani 1 1 d . . .
H6 H 0.9906 0.4364 1.0002 0.039 Uiso 1 1 calc R U .
C7 C 0.7913(5) 0.4419(2) 1.0550(3) 0.0314(9) Uani 1 1 d . . .
C8 C 0.8764(6) 0.4586(2) 1.1423(3) 0.0435(12) Uani 1 1 d . . .
H8A H 0.8081 0.4845 1.1693 0.065 Uiso 1 1 calc R U .
H8B H 0.9763 0.4786 1.1373 0.065 Uiso 1 1 calc R U .
H8C H 0.9002 0.4234 1.1770 0.065 Uiso 1 1 calc R U .
C9 C 0.6273(5) 0.4349(2) 1.0387(3) 0.0328(10) Uani 1 1 d . . .
H9 H 0.5674 0.4432 1.0825 0.039 Uiso 1 1 calc R U .
C10 C 0.5476(5) 0.41604(19) 0.9603(3) 0.0299(9) Uani 1 1 d . . .
C11 C 0.3694(6) 0.4062(3) 0.9449(3) 0.0427(12) Uani 1 1 d . . .
H11A H 0.3249 0.4196 0.9945 0.064 Uiso 1 1 calc R U .
H11B H 0.3472 0.3646 0.9360 0.064 Uiso 1 1 calc R U .
H11C H 0.3203 0.4280 0.8943 0.064 Uiso 1 1 calc R U .
C12 C 0.5000 0.5873(3) 0.7500 0.0278(12) Uani 1 2 d S T P
C13 C 0.3736(6) 0.6206(2) 0.7097(3) 0.0385(11) Uani 1 1 d . . .
C14 C 0.3708(9) 0.6808(3) 0.7102(4) 0.0610(17) Uani 1 1 d . . .
C15 C 0.5000 0.7108(3) 0.7500 0.066(3) Uani 1 2 d S T P
F1 F 0.2430(4) 0.59359(17) 0.6673(2) 0.0636(10) Uani 1 1 d . . .
F2 F 0.2416(7) 0.7103(2) 0.6722(3) 0.1053(18) Uani 1 1 d . . .
F3 F 0.5000 0.7689(2) 0.7500 0.112(3) Uani 1 2 d S T P
N1 N 0.5592(5) 0.38525(15) 0.8146(2) 0.0283(8) Uani 1 1 d . . .
C16 C 0.5901(16) 0.2453(5) 1.0124(8) 0.121(4) Uiso 1 1 d . . .
H16 H 0.4822 0.2419 1.0205 0.145 Uiso 1 1 calc R U .
C17 C 0.6644(13) 0.2103(4) 0.9495(7) 0.100(3) Uiso 1 1 d . . .
H17 H 0.6022 0.1826 0.9142 0.121 Uiso 1 1 calc R U .
C18 C 0.8017(13) 0.2175(4) 0.9439(7) 0.100(3) Uiso 1 1 d . . .
H18 H 0.8407 0.1937 0.9031 0.120 Uiso 1 1 calc R U .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
C1 Cu1 C12 180.0 . .
N1 C1 N1 103.1(5) . 2_656
N1 C1 Cu1 128.4(2) . .
N1 C1 Cu1 128.4(2) 2_656 .
C2 C2 N1 106.5(2) 2_656 .
C2 C2 H2 126.8 2_656 .
N1 C2 H2 126.8 . .
C4 C3 C10 122.6(4) . .
C4 C3 N1 118.4(4) . .
C10 C3 N1 119.1(4) . .
C3 C4 C6 117.8(4) . .
C3 C4 C5 121.0(4) . .
C6 C4 C5 121.2(4) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 C7 121.3(4) . .
C4 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C9 C7 C6 118.7(4) . .
C9 C7 C8 121.0(4) . .
C6 C7 C8 120.2(4) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 C10 122.0(4) . .
C7 C9 H9 119.0 . .
C10 C9 H9 119.0 . .
C9 C10 C3 117.6(4) . .
C9 C10 C11 121.2(4) . .
C3 C10 C11 121.2(4) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C13 112.8(6) 2_656 .
C13 C12 Cu1 123.6(3) 2_656 .
C13 C12 Cu1 123.6(3) . .
F1 C13 C14 116.7(5) . .
F1 C13 C12 119.0(4) . .
C14 C13 C12 124.3(5) . .
F2 C14 C15 119.2(6) . .
F2 C14 C13 121.0(7) . .
C15 C14 C13 119.8(6) . .
F3 C15 C14 120.5(4) . 2_656
F3 C15 C14 120.5(4) . .
C14 C15 C14 119.0(7) 2_656 .
C1 N1 C2 111.9(4) . .
C1 N1 C3 123.2(3) . .
C2 N1 C3 124.9(3) . .
C18 C16 C17 110.8(11) 7_657 .
C18 C16 H16 124.6 7_657 .
C17 C16 H16 124.6 . .
C18 C17 C16 120.0(11) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C16 129.2(12) . 7_657
C17 C18 H18 115.4 . .
C16 C18 H18 115.4 7_657 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C1 1.888(6) .
Cu1 C12 1.907(6) .
C1 N1 1.361(5) .
C1 N1 1.361(5) 2_656
C2 C2 1.351(9) 2_656
C2 N1 1.377(6) .
C2 H2 0.9500 .
C3 C4 1.388(6) .
C3 C10 1.391(6) .
C3 N1 1.444(5) .
C4 C6 1.394(6) .
C4 C5 1.513(6) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.391(6) .
C6 H6 0.9500 .
C7 C9 1.382(6) .
C7 C8 1.504(6) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.386(6) .
C9 H9 0.9500 .
C10 C11 1.508(6) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.386(6) 2_656
C12 C13 1.386(6) .
C13 F1 1.349(6) .
C13 C14 1.382(8) .
C14 F2 1.343(7) .
C14 C15 1.359(8) .
C15 F3 1.335(9) .
C15 C14 1.359(8) 2_656
C16 C18 1.358(14) 7_657
C16 C17 1.503(14) .
C16 H16 0.9500 .
C17 C18 1.195(13) .
C17 H17 0.9500 .
C18 C16 1.358(14) 7_657
C18 H18 0.9500 .
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_4
C10 C3 C4 C6 0.3(6) . .
N1 C3 C4 C6 -179.5(4) . .
C10 C3 C4 C5 178.9(4) . .
N1 C3 C4 C5 -0.9(6) . .
C3 C4 C6 C7 0.3(7) . .
C5 C4 C6 C7 -178.3(4) . .
C4 C6 C7 C9 -1.2(7) . .
C4 C6 C7 C8 176.3(4) . .
C6 C7 C9 C10 1.5(7) . .
C8 C7 C9 C10 -175.9(5) . .
C7 C9 C10 C3 -1.0(7) . .
C7 C9 C10 C11 177.3(5) . .
C4 C3 C10 C9 0.1(7) . .
N1 C3 C10 C9 179.9(4) . .
C4 C3 C10 C11 -178.2(4) . .
N1 C3 C10 C11 1.6(6) . .
C13 C12 C13 F1 179.5(5) 2_656 .
Cu1 C12 C13 F1 -0.5(5) . .
C13 C12 C13 C14 -1.1(4) 2_656 .
Cu1 C12 C13 C14 178.9(4) . .
F1 C13 C14 F2 1.8(8) . .
C12 C13 C14 F2 -177.6(5) . .
F1 C13 C14 C15 -178.4(4) . .
C12 C13 C14 C15 2.2(8) . .
F2 C14 C15 F3 -1.2(7) . .
C13 C14 C15 F3 179.0(4) . .
F2 C14 C15 C14 178.8(7) . 2_656
C13 C14 C15 C14 -1.0(4) . 2_656
N1 C1 N1 C2 -0.4(3) 2_656 .
Cu1 C1 N1 C2 179.6(3) . .
N1 C1 N1 C3 178.6(5) 2_656 .
Cu1 C1 N1 C3 -1.4(5) . .
C2 C2 N1 C1 1.1(7) 2_656 .
C2 C2 N1 C3 -177.9(5) 2_656 .
C4 C3 N1 C1 -91.0(5) . .
C10 C3 N1 C1 89.2(5) . .
C4 C3 N1 C2 87.9(6) . .
C10 C3 N1 C2 -91.9(6) . .
C18 C16 C17 C18 0.3(18) 7_657 .
C16 C17 C18 C16 0(2) . 7_657
