#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:01:21 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178709 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/20/4082025.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_4082025
loop_
_publ_author_name
'Liu, Yanpin'
'Chen, Chaohuang'
'Li, Huaifeng'
'Huang, Kuo-Wei'
'Tan, Jianwei'
'Weng, Zhiqiang'
_publ_section_title
;
 Efficient SN2 Fluorination of Primary and Secondary Alkyl Bromides by
 Copper(I) Fluoride Complexes
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6587
_journal_paper_doi               10.1021/om4008967
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C28 H27 Cu F2 N4 O'
_chemical_formula_weight         537.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.352(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2092(13)
_cell_length_b                   11.3656(8)
_cell_length_c                   12.8405(9)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.17
_cell_volume                     2421.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8433
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.9112
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0659P)²+0.7067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2453
_reflns_number_total             2776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4008967_si_004.cif
_cod_data_source_block           9188
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4082025
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.365135(12) 0.2500 0.03578(4) Uani 1 2 d S . .
N1 N 0.10149(3) 0.27899(5) 0.26163(5) 0.02994(16) Uani 1 1 d . . .
N2 N 0.08314(4) 0.46849(6) 0.37440(5) 0.03165(17) Uani 1 1 d . . .
C1 C 0.10937(5) 0.18069(7) 0.21000(6) 0.0358(2) Uani 1 1 d . . .
C2 C 0.18535(5) 0.13348(7) 0.23059(7) 0.0418(2) Uani 1 1 d . . .
H2 H 0.1890 0.0642 0.1945 0.050 Uiso 1 1 calc R . .
C3 C 0.25394(5) 0.18870(8) 0.30331(7) 0.0411(2) Uani 1 1 d . . .
H3 H 0.3043 0.1588 0.3149 0.049 Uiso 1 1 calc R . .
C4 C 0.24770(4) 0.29151(7) 0.36068(6) 0.0346(2) Uani 1 1 d . . .
C5 C 0.31591(5) 0.35364(8) 0.44029(7) 0.0407(2) Uani 1 1 d . . .
H5 H 0.3674 0.3267 0.4547 0.049 Uiso 1 1 calc R . .
C6 C 0.30742(5) 0.45053(8) 0.49511(7) 0.0401(2) Uani 1 1 d . . .
H6 H 0.3529 0.4891 0.5468 0.048 Uiso 1 1 calc R . .
C7 C 0.22862(4) 0.49425(7) 0.47403(6) 0.0345(2) Uani 1 1 d . . .
C8 C 0.21540(5) 0.59621(8) 0.52642(7) 0.0448(3) Uani 1 1 d . . .
H8 H 0.2587 0.6388 0.5782 0.054 Uiso 1 1 calc R . .
C9 C 0.13817(6) 0.63140(7) 0.49991(8) 0.0477(3) Uani 1 1 d . . .
H9 H 0.1290 0.6996 0.5328 0.057 Uiso 1 1 calc R . .
C10 C 0.07235(5) 0.56650(7) 0.42387(7) 0.0384(2) Uani 1 1 d . . .
C11 C 0.16004(4) 0.43433(6) 0.39671(6) 0.02980(19) Uani 1 1 d . . .
C12 C 0.16981(4) 0.33176(7) 0.33774(6) 0.02898(19) Uani 1 1 d . . .
C13 C 0.03438(6) 0.12327(7) 0.12616(8) 0.0480(3) Uani 1 1 d . . .
H13A H -0.0118 0.1682 0.1204 0.072 Uiso 1 1 calc R . .
H13B H 0.0304 0.0450 0.1516 0.072 Uiso 1 1 calc R . .
H13C H 0.0363 0.1197 0.0526 0.072 Uiso 1 1 calc R . .
C14 C -0.01244(6) 0.60387(8) 0.39590(8) 0.0494(3) Uani 1 1 d . . .
H14A H -0.0280 0.6638 0.3381 0.074 Uiso 1 1 calc R . .
H14B H -0.0160 0.6343 0.4634 0.074 Uiso 1 1 calc R . .
H14C H -0.0478 0.5374 0.3682 0.074 Uiso 1 1 calc R . .
F1 F 0.38427(3) 0.33598(13) 0.25066(4) 0.0837(5) Uani 0.50 1 d PD A -1
F2 F 0.46921(3) 0.36929(10) 0.16414(7) 0.0697(5) Uani 0.50 1 d PD B -1
H1F H 0.41285(2) 0.35182(18) 0.18467(4) 0.084 Uiso 0.50 1 d PD C -1
O1W O 0.60418(9) 0.35478(17) 0.28172(13) 0.0959(8) Uani 0.50 1 d PDU D -2
H1O H 0.57950(16) 0.3603(19) 0.3251(2) 0.115 Uiso 0.50 1 d PD E -2
H2O H 0.55929(19) 0.358(2) 0.2238(3) 0.115 Uiso 0.50 1 d PD F -2
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'
O O 0.0106 0.0060 '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
N1 Cu1 N1 122.69(4) 2 .
N1 Cu1 N2 82.12(3) 2 2
N1 Cu1 N2 133.23(3) . 2
N1 Cu1 N2 133.23(3) 2 .
N1 Cu1 N2 82.12(3) . .
N2 Cu1 N2 110.33(3) 2 .
C1 N1 C12 118.06(7) . .
C1 N1 Cu1 130.05(5) . .
C12 N1 Cu1 111.85(5) . .
C10 N2 C11 118.46(6) . .
C10 N2 Cu1 129.79(5) . .
C11 N2 Cu1 111.32(5) . .
N1 C1 C2 121.67(7) . .
N1 C1 C13 117.97(7) . .
C2 C1 C13 120.34(8) . .
C3 C2 C1 120.38(8) . .
C2 C3 C4 119.34(8) . .
C12 C4 C3 116.95(6) . .
C12 C4 C5 119.69(8) . .
C3 C4 C5 123.36(8) . .
C6 C5 C4 121.60(8) . .
C5 C6 C7 120.31(7) . .
C11 C7 C8 117.21(7) . .
C11 C7 C6 119.49(7) . .
C8 C7 C6 123.30(7) . .
C9 C8 C7 118.92(7) . .
C8 C9 C10 121.11(9) . .
N2 C10 C9 121.21(8) . .
N2 C10 C14 117.53(7) . .
C9 C10 C14 121.26(8) . .
N2 C11 C7 123.01(7) . .
N2 C11 C12 117.27(6) . .
C7 C11 C12 119.72(7) . .
N1 C12 C4 123.52(7) . .
N1 C12 C11 117.31(7) . .
C4 C12 C11 119.17(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.0418(7) 2
Cu1 N1 2.0418(7) .
Cu1 N2 2.0564(6) 2
Cu1 N2 2.0565(6) .
N1 C1 1.3366(11) .
N1 C12 1.3637(8) .
N2 C10 1.3364(11) .
N2 C11 1.3649(10) .
C1 C2 1.4037(13) .
C1 C13 1.4957(11) .
C2 C3 1.3653(11) .
C3 C4 1.4107(12) .
C4 C12 1.4011(11) .
C4 C5 1.4280(10) .
C5 C6 1.3497(13) .
C6 C7 1.4348(12) .
C7 C11 1.4093(9) .
C7 C8 1.4097(13) .
C8 C9 1.3632(14) .
C9 C10 1.4032(11) .
C10 C14 1.4953(13) .
C11 C12 1.4405(11) .
