#------------------------------------------------------------------------------
#$Date: 2019-11-23 10:58:49 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/30/1553029.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_1553029
loop_
_publ_author_name
'Cao, Yanchun'
'Zhang, Yanlu'
'Zhang, Lei'
'Zhang, Dan'
'Leng, Xuebing'
'Huang, Zheng'
_publ_section_title
;
 Selective synthesis of secondary benzylic (Z)-allylboronates by
 Fe-catalyzed 1,4-hydroboration of 1-aryl-substituted 1,3-dienes
;
_journal_issue                   9
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              1101
_journal_paper_doi               10.1039/C4QO00206G
_journal_volume                  1
_journal_year                    2014
_chemical_formula_sum            'C20 H26 Cl2 Fe N2'
_chemical_formula_weight         421.18
_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                 90.178(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0055(13)
_cell_length_b                   15.940(2)
_cell_length_c                   14.422(2)
_cell_measurement_reflns_used    4062
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      32.81
_cell_measurement_theta_min      2.56
_cell_volume                     2070.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      140(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0902
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23426
_diffrn_reflns_theta_full        33.11
_diffrn_reflns_theta_max         33.11
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.8417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         7729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0375P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                4939
_reflns_number_total             7729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00206g2.cif
_cod_data_source_block           dm13109
_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/RSC/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_cell_volume        2070.3(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1553029
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
Fe1 Fe 0.93286(3) 0.394769(17) 0.18860(2) 0.01788(8) Uani 1 1 d .
Cl1 Cl 0.96312(6) 0.50910(3) 0.27585(5) 0.03092(14) Uani 1 1 d .
Cl2 Cl 1.06292(6) 0.37760(4) 0.05874(4) 0.03283(14) Uani 1 1 d .
N1 N 0.91060(18) 0.28300(10) 0.26584(12) 0.0179(3) Uani 1 1 d .
N2 N 0.70075(18) 0.37416(10) 0.18670(13) 0.0184(3) Uani 1 1 d .
C1 C 1.0349(2) 0.23208(12) 0.29773(15) 0.0199(4) Uani 1 1 d .
C2 C 1.1070(2) 0.25481(13) 0.38125(16) 0.0220(4) Uani 1 1 d .
C3 C 1.2257(2) 0.20404(14) 0.40965(17) 0.0268(5) Uani 1 1 d .
H3 H 1.2766 0.2170 0.4656 0.032 Uiso 1 1 calc R
C4 C 1.2703(2) 0.13585(13) 0.35845(18) 0.0273(5) Uani 1 1 d .
H4 H 1.3494 0.1015 0.3801 0.033 Uiso 1 1 calc R
C5 C 1.2001(2) 0.11721(13) 0.27534(18) 0.0274(5) Uani 1 1 d .
H5 H 1.2342 0.0712 0.2394 0.033 Uiso 1 1 calc R
C6 C 1.0799(2) 0.16491(12) 0.24334(16) 0.0224(4) Uani 1 1 d .
C7 C 1.0063(2) 0.14068(13) 0.15129(16) 0.0246(5) Uani 1 1 d .
H7 H 0.9262 0.1825 0.1380 0.029 Uiso 1 1 calc R
C8 C 1.1164(3) 0.14302(16) 0.07109(19) 0.0366(6) Uani 1 1 d .
H8A H 1.1953 0.1018 0.0821 0.055 Uiso 1 1 calc R
H8B H 1.1600 0.1992 0.0666 0.055 Uiso 1 1 calc R
H8C H 1.0647 0.1295 0.0131 0.055 Uiso 1 1 calc R
C9 C 0.9343(3) 0.05384(15) 0.1579(2) 0.0389(6) Uani 1 1 d .
H9A H 0.8839 0.0408 0.0993 0.058 Uiso 1 1 calc R
H9B H 0.8618 0.0536 0.2085 0.058 Uiso 1 1 calc R
H9C H 1.0110 0.0116 0.1702 0.058 Uiso 1 1 calc R
C10 C 1.0639(3) 0.33065(14) 0.43852(17) 0.0278(5) Uani 1 1 d .
H10 H 0.9749 0.3570 0.4088 0.033 Uiso 1 1 calc R
C11 C 1.0213(3) 0.30455(18) 0.5359(2) 0.0479(7) Uani 1 1 d .
H11A H 0.9421 0.2625 0.5330 0.072 Uiso 1 1 calc R
H11B H 0.9864 0.3537 0.5704 0.072 Uiso 1 1 calc R
H11C H 1.1081 0.2806 0.5674 0.072 Uiso 1 1 calc R
C12 C 1.1876(3) 0.39607(15) 0.4414(2) 0.0399(6) Uani 1 1 d .
H12A H 1.1531 0.4458 0.4750 0.060 Uiso 1 1 calc R
H12B H 1.2146 0.4119 0.3780 0.060 Uiso 1 1 calc R
H12C H 1.2746 0.3725 0.4730 0.060 Uiso 1 1 calc R
C13 C 0.7359(3) 0.19326(14) 0.35199(18) 0.0309(5) Uani 1 1 d .
H13A H 0.8261 0.1686 0.3787 0.046 Uiso 1 1 calc R
H13B H 0.6810 0.1502 0.3176 0.046 Uiso 1 1 calc R
H13C H 0.6734 0.2154 0.4018 0.046 Uiso 1 1 calc R
C14 C 0.7772(2) 0.26251(12) 0.28807(15) 0.0191(4) Uani 1 1 d .
C15 C 0.6560(2) 0.31279(12) 0.24485(15) 0.0199(4) Uani 1 1 d .
C16 C 0.5080(2) 0.29630(14) 0.26024(17) 0.0277(5) Uani 1 1 d .
H16 H 0.4786 0.2541 0.3029 0.033 Uiso 1 1 calc R
C17 C 0.4024(2) 0.34294(15) 0.21187(18) 0.0307(5) Uani 1 1 d .
H17 H 0.2996 0.3322 0.2201 0.037 Uiso 1 1 calc R
C18 C 0.4483(2) 0.40450(14) 0.15227(18) 0.0292(5) Uani 1 1 d .
H18 H 0.3773 0.4365 0.1187 0.035 Uiso 1 1 calc R
C19 C 0.5991(2) 0.41993(13) 0.14112(16) 0.0221(4) Uani 1 1 d .
C20 C 0.6565(3) 0.48628(14) 0.07667(17) 0.0286(5) Uani 1 1 d .
H20A H 0.7484 0.5101 0.1020 0.043 Uiso 1 1 calc R
H20B H 0.5820 0.5307 0.0700 0.043 Uiso 1 1 calc R
H20C H 0.6765 0.4614 0.0159 0.043 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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
N1 Fe1 N2 77.32(6)
N1 Fe1 Cl2 113.00(5)
N2 Fe1 Cl2 119.45(5)
N1 Fe1 Cl1 113.79(5)
N2 Fe1 Cl1 104.66(5)
Cl2 Fe1 Cl1 120.71(3)
C14 N1 C1 119.81(17)
C14 N1 Fe1 115.85(13)
C1 N1 Fe1 124.27(12)
C19 N2 C15 119.58(17)
C19 N2 Fe1 126.49(14)
C15 N2 Fe1 113.63(13)
C6 C1 C2 122.98(19)
C6 C1 N1 118.51(19)
C2 C1 N1 118.49(18)
C3 C2 C1 116.7(2)
C3 C2 C10 119.9(2)
C1 C2 C10 123.42(18)
C4 C3 C2 121.6(2)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 120.1(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 121.3(2)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 117.4(2)
C1 C6 C7 123.89(19)
C5 C6 C7 118.74(19)
C8 C7 C9 110.2(2)
C8 C7 C6 111.73(19)
C9 C7 C6 110.86(19)
C8 C7 H7 108.0
C9 C7 H7 108.0
C6 C7 H7 108.0
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 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C2 110.63(19)
C11 C10 C12 110.4(2)
C2 C10 C12 111.80(19)
C11 C10 H10 107.9
C2 C10 H10 107.9
C12 C10 H10 107.9
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
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 H13A 109.5
C14 C13 H13B 109.5
H13A C13 H13B 109.5
C14 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N1 C14 C13 125.37(19)
N1 C14 C15 116.29(18)
C13 C14 C15 118.34(18)
N2 C15 C16 121.9(2)
N2 C15 C14 115.46(17)
C16 C15 C14 122.6(2)
C15 C16 C17 118.5(2)
C15 C16 H16 120.8
C17 C16 H16 120.8
C18 C17 C16 119.4(2)
C18 C17 H17 120.3
C16 C17 H17 120.3
C17 C18 C19 119.8(2)
C17 C18 H18 120.1
C19 C18 H18 120.1
N2 C19 C18 120.9(2)
N2 C19 C20 116.80(18)
C18 C19 C20 122.3(2)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N1 2.1111(16)
Fe1 N2 2.1160(17)
Fe1 Cl2 2.2289(7)
Fe1 Cl1 2.2309(7)
N1 C14 1.286(2)
N1 C1 1.456(3)
N2 C19 1.341(3)
N2 C15 1.351(3)
C1 C6 1.389(3)
C1 C2 1.414(3)
C2 C3 1.401(3)
C2 C10 1.515(3)
C3 C4 1.375(3)
C3 H3 0.9500
C4 C5 1.386(3)
C4 H4 0.9500
C5 C6 1.400(3)
C5 H5 0.9500
C6 C7 1.532(3)
C7 C8 1.526(3)
C7 C9 1.532(3)
C7 H7 1.0000
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.516(4)
C10 C12 1.527(3)
C10 H10 1.0000
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.486(3)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.489(3)
C15 C16 1.377(3)
C16 C17 1.393(3)
C16 H16 0.9500
C17 C18 1.369(3)
C17 H17 0.9500
C18 C19 1.390(3)
C18 H18 0.9500
C19 C20 1.501(3)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
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
N2 Fe1 N1 C14 -10.37(15)
Cl2 Fe1 N1 C14 -127.25(15)
Cl1 Fe1 N1 C14 90.24(16)
N2 Fe1 N1 C1 172.58(17)
Cl2 Fe1 N1 C1 55.71(17)
Cl1 Fe1 N1 C1 -86.80(16)
N1 Fe1 N2 C19 -176.07(19)
Cl2 Fe1 N2 C19 -66.62(18)
Cl1 Fe1 N2 C19 72.31(18)
N1 Fe1 N2 C15 10.17(14)
Cl2 Fe1 N2 C15 119.61(14)
Cl1 Fe1 N2 C15 -101.46(14)
C14 N1 C1 C6 88.7(2)
Fe1 N1 C1 C6 -94.4(2)
C14 N1 C1 C2 -93.2(2)
Fe1 N1 C1 C2 83.7(2)
C6 C1 C2 C3 -2.2(3)
N1 C1 C2 C3 179.79(18)
C6 C1 C2 C10 176.7(2)
N1 C1 C2 C10 -1.3(3)
C1 C2 C3 C4 0.4(3)
C10 C2 C3 C4 -178.5(2)
C2 C3 C4 C5 1.7(3)
C3 C4 C5 C6 -2.3(3)
C2 C1 C6 C5 1.7(3)
N1 C1 C6 C5 179.69(18)
C2 C1 C6 C7 -178.17(19)
N1 C1 C6 C7 -0.2(3)
C4 C5 C6 C1 0.6(3)
C4 C5 C6 C7 -179.5(2)
C1 C6 C7 C8 120.8(2)
C5 C6 C7 C8 -59.1(3)
C1 C6 C7 C9 -115.9(2)
C5 C6 C7 C9 64.3(3)
C3 C2 C10 C11 -59.6(3)
C1 C2 C10 C11 121.5(2)
C3 C2 C10 C12 63.9(3)
C1 C2 C10 C12 -115.0(2)
C1 N1 C14 C13 5.5(3)
Fe1 N1 C14 C13 -171.67(17)
C1 N1 C14 C15 -174.03(18)
Fe1 N1 C14 C15 8.8(2)
C19 N2 C15 C16 -1.1(3)
Fe1 N2 C15 C16 173.18(17)
C19 N2 C15 C14 176.74(18)
Fe1 N2 C15 C14 -9.0(2)
N1 C14 C15 N2 0.3(3)
C13 C14 C15 N2 -179.30(19)
N1 C14 C15 C16 178.1(2)
C13 C14 C15 C16 -1.5(3)
N2 C15 C16 C17 2.0(3)
C14 C15 C16 C17 -175.6(2)
C15 C16 C17 C18 -1.3(4)
C16 C17 C18 C19 -0.3(4)
C15 N2 C19 C18 -0.6(3)
Fe1 N2 C19 C18 -174.05(16)
C15 N2 C19 C20 -179.19(19)
Fe1 N2 C19 C20 7.4(3)
C17 C18 C19 N2 1.3(3)
C17 C18 C19 C20 179.8(2)
