#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:41:20 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236069 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/73/4037391.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_4037391
loop_
_publ_author_name
'Debbarma, Suvankar'
'Bera, Sourav Sekhar'
'Maji, Modhu Sudan'
_publ_section_title
;
 Cp*Rh(III)-Catalyzed Low Temperature C-H Allylation of N-Aryl-trichloro
 Acetimidamide.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11716
_journal_page_last               11725
_journal_paper_doi               10.1021/acs.joc.6b02150
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C13 H13 Cl3 N2 O2'
_chemical_formula_weight         335.60
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.376(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.206(5)
_cell_length_b                   10.587(5)
_cell_length_c                   22.580(5)
_cell_measurement_reflns_used    2258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1.8
_cell_volume                     1481.0(14)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18613
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.9406
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0583
_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)+(0.1272P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.2051
_reflns_number_gt                2151
_reflns_number_total             3202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02150_si_002.cif
_cod_data_source_block           monop21n
_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/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      P21/n
_cod_database_code               4037391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl1 Cl -0.14449(16) 0.34705(9) 0.08763(4) 0.0311(3) Uani 1 1 d .
Cl2 Cl -0.12043(17) 0.15609(10) -0.00219(4) 0.0344(3) Uani 1 1 d .
Cl3 Cl 0.17771(19) 0.36768(9) 0.00111(5) 0.0402(3) Uani 1 1 d .
O1 O -0.3872(4) -0.1277(2) 0.08659(12) 0.0294(7) Uani 1 1 d .
O2 O -0.3713(4) -0.3140(2) 0.13422(12) 0.0284(6) Uani 1 1 d .
N1 N 0.1715(5) 0.1767(3) 0.13901(15) 0.0275(8) Uani 1 1 d .
H1 H 0.0803 0.2258 0.1547 0.033 Uiso 1 1 calc R
N2 N 0.3392(5) 0.1128(3) 0.05295(14) 0.0285(8) Uani 1 1 d .
H2 H 0.3194 0.1257 0.0204 0.043 Uiso 1 1 calc R
C12 C 0.1948(6) 0.1798(3) 0.08402(17) 0.0234(8) Uani 1 1 d .
C7 C 0.0095(6) -0.0675(4) 0.15330(17) 0.0273(8) Uani 1 1 d .
H7 H -0.0627 -0.0048 0.1312 0.033 Uiso 1 1 calc R
C2 C 0.2152(6) -0.0316(3) 0.18457(17) 0.0254(8) Uani 1 1 d .
C6 C 0.4941(7) 0.1273(4) 0.20223(18) 0.0304(9) Uani 1 1 d .
H6 H 0.5482 0.2075 0.1952 0.036 Uiso 1 1 calc R
C1 C 0.2974(6) 0.0912(3) 0.17466(17) 0.0255(8) Uani 1 1 d .
C8 C -0.0840(6) -0.1811(4) 0.15352(17) 0.0272(9) Uani 1 1 d .
H8 H -0.0163 -0.2475 0.1741 0.033 Uiso 1 1 calc R
C10 C -0.5858(6) -0.3466(4) 0.10892(19) 0.0296(9) Uani 1 1 d .
H10A H -0.5796 -0.3680 0.0673 0.036 Uiso 1 1 calc R
H10B H -0.6836 -0.2758 0.1123 0.036 Uiso 1 1 calc R
C9 C -0.2945(6) -0.2015(4) 0.12109(18) 0.0263(8) Uani 1 1 d .
C4 C 0.5304(6) -0.0735(4) 0.25072(17) 0.0297(9) Uani 1 1 d .
H4 H 0.6077 -0.1283 0.2762 0.036 Uiso 1 1 calc R
C5 C 0.6104(6) 0.0461(4) 0.23981(18) 0.0311(9) Uani 1 1 d .
H5 H 0.7421 0.0716 0.2578 0.037 Uiso 1 1 calc R
C3 C 0.3338(6) -0.1112(4) 0.22334(18) 0.0280(9) Uani 1 1 d .
H3 H 0.2804 -0.1912 0.2311 0.034 Uiso 1 1 calc R
C13 C 0.0361(6) 0.2604(4) 0.04528(16) 0.0276(9) Uani 1 1 d .
C11 C -0.6627(8) -0.4586(4) 0.1433(2) 0.0420(11) Uani 1 1 d .
H11A H -0.8042 -0.4827 0.1280 0.063 Uiso 1 1 calc R
H11B H -0.6678 -0.4362 0.1844 0.063 Uiso 1 1 calc R
H11C H -0.5648 -0.5279 0.1395 0.063 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'
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
C9 O2 C10 117.2(3)
C12 N1 C1 119.1(3)
N1 C12 N2 127.5(4)
N1 C12 C13 118.0(3)
N2 C12 C13 114.4(3)
C8 C7 C2 126.6(4)
C3 C2 C1 118.1(3)
C3 C2 C7 123.8(3)
C1 C2 C7 118.1(3)
C5 C6 C1 121.1(4)
C6 C1 N1 121.3(3)
C6 C1 C2 119.7(4)
N1 C1 C2 118.9(3)
C7 C8 C9 120.1(4)
O2 C10 C11 107.0(3)
O1 C9 O2 123.7(4)
O1 C9 C8 126.4(3)
O2 C9 C8 109.9(3)
C5 C4 C3 119.7(4)
C6 C5 C4 119.8(4)
C2 C3 C4 121.5(4)
C12 C13 Cl1 112.6(3)
C12 C13 Cl3 110.6(3)
Cl1 C13 Cl3 108.8(2)
C12 C13 Cl2 107.8(3)
Cl1 C13 Cl2 107.8(2)
Cl3 C13 Cl2 109.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.771(4)
Cl2 C13 1.786(4)
Cl3 C13 1.778(4)
O1 C9 1.223(5)
O2 C9 1.324(4)
O2 C10 1.459(5)
N1 C12 1.259(5)
N1 C1 1.416(5)
N2 C12 1.369(5)
C12 C13 1.537(5)
C7 C8 1.335(5)
C7 C2 1.472(6)
C2 C3 1.393(5)
C2 C1 1.419(5)
C6 C5 1.381(6)
C6 C1 1.391(6)
C8 C9 1.475(6)
C10 C11 1.510(5)
C4 C5 1.388(6)
C4 C3 1.393(6)
