#------------------------------------------------------------------------------
#$Date: 2019-11-25 10:20:10 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240664 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/00/4130086.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_4130086
loop_
_publ_author_name
'Xu, Long'
'Vicic, David A.'
_publ_section_title
;
 Direct Difluoromethylation of Aryl Halides via Base Metal Catalysis at
 Room Temperature.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2536
_journal_page_last               2539
_journal_paper_doi               10.1021/jacs.6b00053
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C14 H26 F4 N4 O2 Zn'
_chemical_formula_weight         423.76
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 128.5440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0565(14)
_cell_length_b                   9.8443(8)
_cell_length_c                   13.4192(10)
_cell_measurement_reflns_used    17021
_cell_measurement_temperature    145(2)
_cell_measurement_theta_max      30.62
_cell_measurement_theta_min      2.88
_cell_volume                     1865.6(3)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      145(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17021
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.616
_diffrn_reflns_theta_min         2.885
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       platelet
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.188
_refine_diff_density_min         -1.180
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.0034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0736P)²+5.0685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2433
_reflns_number_total             2585
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b00053_si_002.cif
_cod_data_source_block           Compound1
_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               4130086
_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   0.684
_shelx_estimated_absorpt_t_max   0.973
_shelxl_version_number           2014/6
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
Zn1 Zn 0.5000 0.69618(4) 0.2500 0.03003(17) Uani 1 2 d S T P
O1 O 0.51517(15) 0.8396(2) 0.37385(19) 0.0361(4) Uani 1 1 d . . .
F2 F 0.34613(17) 0.6169(3) 0.2475(2) 0.0662(7) Uani 1 1 d . . .
F1 F 0.35875(17) 0.4831(2) 0.1305(3) 0.0698(7) Uani 1 1 d . . .
N1 N 0.39229(16) 0.9056(3) 0.3668(2) 0.0385(5) Uani 1 1 d . . .
N2 N 0.50731(18) 0.7599(3) 0.5240(2) 0.0406(5) Uani 1 1 d . . .
C1 C 0.36885(18) 0.6158(3) 0.1663(3) 0.0338(5) Uani 1 1 d . . .
H1A H 0.3208 0.6712 0.0893 0.041 Uiso 1 1 calc R U .
C2 C 0.47202(17) 0.8341(3) 0.4193(2) 0.0288(5) Uani 1 1 d . . .
C6 C 0.3489(3) 0.9755(4) 0.2479(3) 0.0595(10) Uani 1 1 d . . .
H6A H 0.3924 0.9757 0.2275 0.089 Uiso 1 1 calc R U .
H6B H 0.3347 1.0693 0.2553 0.089 Uiso 1 1 calc R U .
H6C H 0.2901 0.9291 0.1799 0.089 Uiso 1 1 calc R U .
C3 C 0.3370(2) 0.8957(6) 0.4127(4) 0.0729(14) Uani 1 1 d . . .
H3A H 0.3261 0.9883 0.4298 0.087 Uiso 1 1 calc R U .
H3B H 0.2745 0.8556 0.3446 0.087 Uiso 1 1 calc R U .
C7 C 0.5925(3) 0.6807(5) 0.5768(5) 0.0718(13) Uani 1 1 d . . .
H7A H 0.6383 0.7361 0.5784 0.108 Uiso 1 1 calc R U .
H7B H 0.5763 0.6001 0.5239 0.108 Uiso 1 1 calc R U .
H7C H 0.6202 0.6524 0.6637 0.108 Uiso 1 1 calc R U .
C5 C 0.4558(4) 0.7328(7) 0.5717(5) 0.0832(16) Uani 1 1 d . . .
H5A H 0.4328 0.6378 0.5507 0.100 Uiso 1 1 calc R U .
H5B H 0.4999 0.7410 0.6657 0.100 Uiso 1 1 calc R U .
C4 C 0.3810(7) 0.8163(7) 0.5248(10) 0.146(4) Uani 1 1 d . . .
H4B H 0.4008 0.8806 0.5942 0.175 Uiso 1 1 calc R U .
H4A H 0.3305 0.7592 0.5118 0.175 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'
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'
Zn Zn 0.2839 1.4301 '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 Zn1 C1 134.49(16) 2_655 .
C1 Zn1 O1 103.53(9) 2_655 2_655
C1 Zn1 O1 107.16(10) . 2_655
C1 Zn1 O1 107.16(10) 2_655 .
C1 Zn1 O1 103.53(9) . .
O1 Zn1 O1 93.72(12) 2_655 .
C2 O1 Zn1 123.43(17) . .
C2 N1 C6 119.8(3) . .
C2 N1 C3 122.2(3) . .
C6 N1 C3 117.0(3) . .
C2 N2 C5 123.2(3) . .
C2 N2 C7 118.1(3) . .
C5 N2 C7 117.5(3) . .
F1 C1 F2 104.1(2) . .
F1 C1 Zn1 114.76(18) . .
F2 C1 Zn1 112.02(18) . .
F1 C1 H1A 108.6 . .
F2 C1 H1A 108.6 . .
Zn1 C1 H1A 108.6 . .
O1 C2 N2 119.9(2) . .
O1 C2 N1 120.7(2) . .
N2 C2 N1 119.3(2) . .
N1 C6 H6A 109.5 . .
N1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C4 C3 N1 113.8(3) . .
C4 C3 H3A 108.8 . .
N1 C3 H3A 108.8 . .
C4 C3 H3B 108.8 . .
N1 C3 H3B 108.8 . .
H3A C3 H3B 107.7 . .
N2 C7 H7A 109.5 . .
N2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C4 C5 N2 114.4(4) . .
C4 C5 H5A 108.7 . .
N2 C5 H5A 108.7 . .
C4 C5 H5B 108.7 . .
N2 C5 H5B 108.7 . .
H5A C5 H5B 107.6 . .
C5 C4 C3 124.3(4) . .
C5 C4 H4B 106.2 . .
C3 C4 H4B 106.2 . .
C5 C4 H4A 106.2 . .
C3 C4 H4A 106.2 . .
H4B C4 H4A 106.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 C1 2.045(2) 2_655
Zn1 C1 2.045(2) .
Zn1 O1 2.0647(19) 2_655
Zn1 O1 2.0647(19) .
O1 C2 1.254(3) .
F2 C1 1.383(3) .
F1 C1 1.364(3) .
N1 C2 1.342(3) .
N1 C6 1.441(4) .
N1 C3 1.467(5) .
N2 C2 1.341(3) .
N2 C5 1.445(4) .
N2 C7 1.455(5) .
C1 H1A 1.0000 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C3 C4 1.420(9) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C5 C4 1.355(8) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C4 H4B 0.9900 .
C4 H4A 0.9900 .
