#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/38/4123872.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_4123872
loop_
_publ_author_name
'Shin, Kwangmin'
'Park, Sung-Woo'
'Chang, Sukbok'
_publ_section_title
;
 Cp*Ir(III)-Catalyzed Mild and Broad C-H Arylation of Arenes and Alkenes
 with Aryldiazonium Salts Leading to the External Oxidant-Free Approach.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8584
_journal_page_last               8592
_journal_paper_doi               10.1021/jacs.5b04043
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C14 H18 Cl N O'
_chemical_formula_sum            'C14 H18 Cl N O'
_chemical_formula_weight         251.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 100.955(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.401(3)
_cell_length_b                   8.6470(17)
_cell_length_c                   9.4509(18)
_cell_measurement_reflns_used    21802
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.38
_cell_volume                     1396.1(5)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21802
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.5613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                2267
_reflns_number_total             2847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b04043_si_003.cif
_cod_data_source_block           0271b-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4123872--4123873.cif.
;
_cod_original_cell_volume        1396.2(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4123872
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
Cl1 Cl 0.04294(2) 1.33214(5) 0.45746(4) 0.03020(13) Uani 1 1 d .
O1 O 0.32137(8) 0.74080(14) 0.85192(12) 0.0385(3) Uani 1 1 d .
N1 N 0.32936(7) 0.85566(14) 0.63934(13) 0.0216(3) Uani 1 1 d .
H1A H 0.3122 0.8514 0.5456 0.026 Uiso 1 1 calc R
C1 C 0.08268(9) 1.14682(17) 0.48570(17) 0.0232(3) Uani 1 1 d .
C2 C 0.07126(9) 1.04167(18) 0.37361(17) 0.0261(3) Uani 1 1 d .
H2A H 0.0430 1.0700 0.2812 0.031 Uiso 1 1 calc R
C3 C 0.10188(9) 0.89388(19) 0.39852(17) 0.0262(4) Uani 1 1 d .
H3A H 0.0938 0.8206 0.3222 0.031 Uiso 1 1 calc R
C4 C 0.14423(9) 0.85047(18) 0.53283(16) 0.0231(3) Uani 1 1 d .
C5 C 0.15361(9) 0.95913(18) 0.64418(16) 0.0243(3) Uani 1 1 d .
H5A H 0.1811 0.9309 0.7373 0.029 Uiso 1 1 calc R
C6 C 0.12354(9) 1.10722(18) 0.62132(16) 0.0245(3) Uani 1 1 d .
H6A H 0.1308 1.1806 0.6975 0.029 Uiso 1 1 calc R
C7 C 0.17448(9) 0.69072(18) 0.55513(17) 0.0264(4) Uani 1 1 d .
H7A H 0.1425 0.6121 0.5041 0.032 Uiso 1 1 calc R
C8 C 0.24095(9) 0.64336(18) 0.63780(17) 0.0258(4) Uani 1 1 d .
C9 C 0.26124(11) 0.47444(19) 0.6610(2) 0.0380(4) Uani 1 1 d .
H9A H 0.2199 0.4112 0.6040 0.057 Uiso 1 1 calc R
H9B H 0.2660 0.4491 0.7633 0.057 Uiso 1 1 calc R
H9C H 0.3110 0.4533 0.6307 0.057 Uiso 1 1 calc R
C10 C 0.30068(9) 0.75178(17) 0.71953(16) 0.0245(3) Uani 1 1 d .
C11 C 0.38730(9) 0.97748(19) 0.69254(16) 0.0259(4) Uani 1 1 d .
C12 C 0.46557(11) 0.9044(2) 0.7567(2) 0.0498(5) Uani 1 1 d .
H12A H 0.4600 0.8422 0.8409 0.075 Uiso 1 1 calc R
H12B H 0.5045 0.9858 0.7861 0.075 Uiso 1 1 calc R
H12C H 0.4827 0.8380 0.6845 0.075 Uiso 1 1 calc R
C13 C 0.35839(11) 1.0791(2) 0.8035(2) 0.0400(5) Uani 1 1 d .
H13A H 0.3082 1.1259 0.7600 0.060 Uiso 1 1 calc R
H13B H 0.3968 1.1608 0.8356 0.060 Uiso 1 1 calc R
H13C H 0.3516 1.0159 0.8864 0.060 Uiso 1 1 calc R
C14 C 0.39405(13) 1.0749(2) 0.5613(2) 0.0469(5) Uani 1 1 d .
H14A H 0.3431 1.1210 0.5215 0.070 Uiso 1 1 calc R
H14B H 0.4108 1.0093 0.4882 0.070 Uiso 1 1 calc R
H14C H 0.4326 1.1572 0.5897 0.070 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0320(2) 0.0215(2) 0.0366(2) 0.00333(17) 0.00529(16) 0.00259(17)
O1 0.0584(8) 0.0377(7) 0.0196(6) 0.0071(5) 0.0077(5) -0.0013(6)
N1 0.0271(7) 0.0212(7) 0.0160(6) -0.0002(5) 0.0031(5) -0.0013(5)
C1 0.0215(8) 0.0195(8) 0.0297(8) 0.0034(6) 0.0075(6) -0.0012(6)
C2 0.0269(8) 0.0268(9) 0.0239(8) 0.0023(7) 0.0033(6) -0.0038(7)
C3 0.0290(8) 0.0249(8) 0.0253(8) -0.0045(7) 0.0065(6) -0.0056(7)
C4 0.0216(8) 0.0213(8) 0.0277(8) 0.0004(6) 0.0083(6) -0.0033(6)
C5 0.0242(8) 0.0256(8) 0.0238(8) 0.0024(7) 0.0063(6) 0.0008(7)
C6 0.0251(8) 0.0240(8) 0.0254(8) -0.0033(6) 0.0074(6) -0.0013(6)
C7 0.0308(9) 0.0194(8) 0.0312(8) -0.0016(7) 0.0116(7) -0.0049(7)
C8 0.0319(9) 0.0199(8) 0.0283(8) 0.0036(6) 0.0126(7) -0.0001(7)
C9 0.0436(11) 0.0211(9) 0.0500(11) 0.0032(8) 0.0107(9) 0.0014(8)
C10 0.0312(8) 0.0210(8) 0.0230(8) 0.0030(6) 0.0095(6) 0.0066(7)
C11 0.0264(8) 0.0246(9) 0.0252(8) -0.0029(7) 0.0009(6) -0.0030(7)
C12 0.0288(10) 0.0478(12) 0.0678(14) -0.0058(11) -0.0038(9) 0.0030(9)
C13 0.0462(11) 0.0323(10) 0.0418(10) -0.0150(8) 0.0086(9) -0.0042(9)
C14 0.0610(13) 0.0406(11) 0.0374(10) 0.0006(9) 0.0052(9) -0.0270(10)
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'
Cl Cl 0.1484 0.1585 '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
C10 N1 C11 126.30(13)
C2 C1 C6 121.37(14)
C2 C1 Cl1 119.47(12)
C6 C1 Cl1 119.15(12)
C1 C2 C3 118.79(15)
C2 C3 C4 121.51(15)
C3 C4 C5 118.11(14)
C3 C4 C7 119.60(14)
C5 C4 C7 122.23(14)
C6 C5 C4 121.19(15)
C5 C6 C1 119.03(14)
C8 C7 C4 128.09(15)
C7 C8 C10 123.34(14)
C7 C8 C9 122.42(15)
C10 C8 C9 114.21(14)
O1 C10 N1 123.94(15)
O1 C10 C8 120.82(14)
N1 C10 C8 115.24(13)
N1 C11 C12 109.94(14)
N1 C11 C14 105.68(12)
C12 C11 C14 110.69(16)
N1 C11 C13 110.58(13)
C12 C11 C13 110.67(15)
C14 C11 C13 109.17(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7456(16)
O1 C10 1.2381(19)
N1 C10 1.3318(19)
N1 C11 1.479(2)
C1 C2 1.381(2)
C1 C6 1.385(2)
C2 C3 1.387(2)
C3 C4 1.393(2)
C4 C5 1.397(2)
C4 C7 1.479(2)
C5 C6 1.385(2)
C7 C8 1.331(2)
C8 C10 1.500(2)
C8 C9 1.509(2)
C11 C12 1.519(2)
C11 C14 1.523(2)
C11 C13 1.525(2)
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
C6 C1 C2 C3 -0.2(2)
Cl1 C1 C2 C3 -178.73(11)
C1 C2 C3 C4 -0.7(2)
C2 C3 C4 C5 1.6(2)
C2 C3 C4 C7 178.85(14)
C3 C4 C5 C6 -1.6(2)
C7 C4 C5 C6 -178.82(14)
C4 C5 C6 C1 0.8(2)
C2 C1 C6 C5 0.2(2)
Cl1 C1 C6 C5 178.68(11)
C3 C4 C7 C8 145.40(17)
C5 C4 C7 C8 -37.5(2)
C4 C7 C8 C10 -3.5(3)
C4 C7 C8 C9 174.38(15)
C11 N1 C10 O1 -2.4(2)
C11 N1 C10 C8 178.59(13)
C7 C8 C10 O1 122.78(18)
C9 C8 C10 O1 -55.3(2)
C7 C8 C10 N1 -58.2(2)
C9 C8 C10 N1 123.72(15)
C10 N1 C11 C12 66.2(2)
C10 N1 C11 C14 -174.26(15)
C10 N1 C11 C13 -56.2(2)
