#------------------------------------------------------------------------------
#$Date: 2017-03-05 06:29:11 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193677 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119657.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_7119657
loop_
_publ_author_name
'Ma, Chaoqun'
'Chen, Jianghui'
'Xing, Dong'
'Sheng, Yuan'
'Hu, Wenhao'
_publ_section_title
;
 Iron catalyzed efficient synthesis of poly-functional primary amines via
 the direct use of ammonia.
;
_journal_issue                   19
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2854
_journal_page_last               2857
_journal_paper_doi               10.1039/c7cc00003k
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C21 H20 N2 O4 S'
_chemical_formula_weight         396.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-05 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7225(7)
_cell_length_b                   10.1995(8)
_cell_length_c                   22.6633(18)
_cell_measurement_temperature    296(2)
_cell_volume                     2016.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23366
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.52(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3548
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0335
_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)+(0.0435P)²+0.4718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                3339
_reflns_number_total             3548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc00003k2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7119657.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7119657
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
S1 S 0.30114(9) 0.89393(6) 0.13183(2) 0.0648(2) Uani 1 1 d U
O1 O 0.3539(3) 0.69972(17) -0.08438(10) 0.0964(7) Uani 1 1 d .
O2 O 0.3591(2) 0.88719(17) -0.13479(6) 0.0624(4) Uani 1 1 d .
O3 O 0.33707(16) 1.03563(11) 0.03689(5) 0.0374(3) Uani 1 1 d .
O4 O 0.60204(16) 0.90904(14) -0.02226(7) 0.0501(4) Uani 1 1 d .
N1 N 0.2681(2) 0.83431(15) 0.01682(7) 0.0446(4) Uani 1 1 d .
H1A H 0.2538 0.7517 0.0221 0.053 Uiso 1 1 calc R
N2 N 0.58092(17) 1.11145(15) -0.06522(7) 0.0367(3) Uani 1 1 d .
C1 C 0.4615(2) 1.20081(18) -0.07717(8) 0.0353(4) Uani 1 1 d .
C2 C 0.4732(3) 1.3220(2) -0.10364(9) 0.0476(5) Uani 1 1 d .
H2A H 0.5666 1.3541 -0.1171 0.057 Uiso 1 1 calc R
C3 C 0.3391(3) 1.3939(2) -0.10926(9) 0.0555(6) Uani 1 1 d .
H3A H 0.3431 1.4758 -0.1272 0.067 Uiso 1 1 calc R
C4 C 0.2013(3) 1.3482(2) -0.08926(10) 0.0538(6) Uani 1 1 d .
H4A H 0.1135 1.3989 -0.0940 0.065 Uiso 1 1 calc R
C5 C 0.1912(2) 1.22616(19) -0.06187(9) 0.0446(5) Uani 1 1 d .
H5A H 0.0979 1.1954 -0.0476 0.054 Uiso 1 1 calc R
C6 C 0.3229(2) 1.15183(16) -0.05645(8) 0.0337(4) Uani 1 1 d .
C7 C 0.3530(2) 1.02258(16) -0.02688(8) 0.0332(4) Uani 1 1 d .
C8 C 0.5276(2) 1.00387(17) -0.03769(8) 0.0354(4) Uani 1 1 d .
C9 C 0.7436(2) 1.1358(2) -0.07687(9) 0.0456(5) Uani 1 1 d .
H9A H 0.8043 1.0843 -0.0495 0.055 Uiso 1 1 calc R
H9B H 0.7654 1.2275 -0.0693 0.055 Uiso 1 1 calc R
C10 C 0.7929(2) 1.1034(2) -0.13866(9) 0.0455(5) Uani 1 1 d .
C11 C 0.7804(3) 0.9776(2) -0.15956(11) 0.0609(6) Uani 1 1 d .
H11A H 0.7393 0.9127 -0.1355 0.073 Uiso 1 1 calc R
C12 C 0.8277(4) 0.9463(3) -0.21548(13) 0.0817(8) Uani 1 1 d .
H12A H 0.8163 0.8609 -0.2291 0.098 Uiso 1 1 calc R
C13 C 0.8906(4) 1.0375(4) -0.25104(14) 0.0871(10) Uani 1 1 d .
H13A H 0.9232 1.0151 -0.2888 0.105 Uiso 1 1 calc R
C14 C 0.9059(4) 1.1637(4) -0.23100(14) 0.0903(10) Uani 1 1 d .
H14A H 0.9497 1.2271 -0.2552 0.108 Uiso 1 1 calc R
C15 C 0.8563(3) 1.1976(3) -0.17460(12) 0.0681(7) Uani 1 1 d .
H15A H 0.8660 1.2835 -0.1613 0.082 Uiso 1 1 calc R
C16 C 0.3010(2) 0.91633(17) 0.06012(8) 0.0402(4) Uani 1 1 d U
C17 C 0.2586(2) 0.89701(18) -0.04033(8) 0.0398(4) Uani 1 1 d .
C18 C 0.3312(3) 0.8135(2) -0.08820(10) 0.0529(5) Uani 1 1 d .
C19 C 0.4156(5) 0.8214(4) -0.18759(12) 0.1054(10) Uani 1 1 d U
H19A H 0.3498 0.7483 -0.1980 0.126 Uiso 1 1 calc R
H19B H 0.5189 0.7889 -0.1814 0.126 Uiso 1 1 calc R
C20 C 0.4133(5) 0.9240(5) -0.23502(14) 0.1191(11) Uani 1 1 d U
H20A H 0.4500 0.8868 -0.2713 0.179 Uiso 1 1 calc R
H20B H 0.4782 0.9958 -0.2237 0.179 Uiso 1 1 calc R
H20C H 0.3104 0.9550 -0.2404 0.179 Uiso 1 1 calc R
C21 C 0.0906(3) 0.9211(2) -0.05601(12) 0.0621(6) Uani 1 1 d .
H21A H 0.0410 0.8388 -0.0637 0.093 Uiso 1 1 calc R
H21B H 0.0847 0.9755 -0.0905 0.093 Uiso 1 1 calc R
H21C H 0.0404 0.9642 -0.0237 0.093 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'
S S 0.1246 0.1234 '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
C18 O2 C19 117.2(2)
C16 O3 C7 108.88(13)
C16 N1 C17 113.43(15)
C16 N1 H1A 123.3
C17 N1 H1A 123.3
C8 N2 C1 111.14(15)
C8 N2 C9 123.84(16)
C1 N2 C9 124.86(16)
C2 C1 C6 122.28(18)
C2 C1 N2 127.48(18)
C6 C1 N2 110.21(15)
C1 C2 C3 116.9(2)
C1 C2 H2A 121.6
C3 C2 H2A 121.6
C4 C3 C2 122.11(19)
C4 C3 H3A 118.9
C2 C3 H3A 118.9
C3 C4 C5 120.5(2)
C3 C4 H4A 119.7
C5 C4 H4A 119.7
C6 C5 C4 118.5(2)
C6 C5 H5A 120.7
C4 C5 H5A 120.7
C5 C6 C1 119.73(16)
C5 C6 C7 131.82(18)
C1 C6 C7 108.30(15)
O3 C7 C6 110.21(14)
O3 C7 C17 102.66(14)
C6 C7 C17 122.92(15)
O3 C7 C8 105.12(14)
C6 C7 C8 102.06(14)
C17 C7 C8 112.80(15)
O4 C8 N2 126.68(18)
O4 C8 C7 125.13(17)
N2 C8 C7 108.17(15)
N2 C9 C10 114.07(16)
N2 C9 H9A 108.7
C10 C9 H9A 108.7
N2 C9 H9B 108.7
C10 C9 H9B 108.7
H9A C9 H9B 107.6
C11 C10 C15 118.7(2)
C11 C10 C9 120.3(2)
C15 C10 C9 120.9(2)
C12 C11 C10 120.9(3)
C12 C11 H11A 119.6
C10 C11 H11A 119.6
C13 C12 C11 121.0(3)
C13 C12 H12A 119.5
C11 C12 H12A 119.5
C12 C13 C14 119.3(3)
C12 C13 H13A 120.3
C14 C13 H13A 120.3
C13 C14 C15 120.4(3)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C10 C15 C14 119.7(3)
C10 C15 H15A 120.2
C14 C15 H15A 120.2
N1 C16 O3 109.19(16)
N1 C16 S1 130.36(14)
O3 C16 S1 120.45(14)
N1 C17 C18 111.57(16)
N1 C17 C21 109.57(17)
C18 C17 C21 108.95(18)
N1 C17 C7 99.10(14)
C18 C17 C7 112.42(16)
C21 C17 C7 114.93(17)
O1 C18 O2 126.0(2)
O1 C18 C17 124.7(2)
O2 C18 C17 109.24(18)
O2 C19 C20 105.2(3)
O2 C19 H19A 110.7
C20 C19 H19A 110.7
O2 C19 H19B 110.7
C20 C19 H19B 110.7
H19A C19 H19B 108.8
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
C17 C21 H21A 109.5
C17 C21 H21B 109.5
H21A C21 H21B 109.5
C17 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C16 1.641(2)
O1 C18 1.180(3)
O2 C18 1.319(3)
O2 C19 1.458(3)
O3 C16 1.363(2)
O3 C7 1.458(2)
O4 C8 1.216(2)
N1 C16 1.321(2)
N1 C17 1.447(3)
N1 H1A 0.8600
N2 C8 1.345(2)
N2 C1 1.410(2)
N2 C9 1.465(2)
C1 C2 1.378(3)
C1 C6 1.390(3)
C2 C3 1.386(3)
C2 H2A 0.9300
C3 C4 1.367(4)
C3 H3A 0.9300
C4 C5 1.394(3)
C4 H4A 0.9300
C5 C6 1.382(3)
C5 H5A 0.9300
C6 C7 1.502(2)
C7 C17 1.553(2)
C7 C8 1.554(3)
C9 C10 1.502(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.372(3)
C10 C15 1.376(3)
C11 C12 1.370(4)
C11 H11A 0.9300
C12 C13 1.347(4)
C12 H12A 0.9300
C13 C14 1.372(5)
C13 H13A 0.9300
C14 C15 1.393(4)
C14 H14A 0.9300
C15 H15A 0.9300
C17 C18 1.518(3)
C17 C21 1.528(3)
C19 C20 1.500(5)
C19 H19A 0.9700
C19 H19B 0.9700
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
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
C8 N2 C1 C2 178.62(19)
C9 N2 C1 C2 3.1(3)
C8 N2 C1 C6 0.5(2)
C9 N2 C1 C6 -175.07(18)
C6 C1 C2 C3 -0.4(3)
N2 C1 C2 C3 -178.36(19)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C5 0.3(3)
C3 C4 C5 C6 -1.2(3)
C4 C5 C6 C1 1.2(3)
C4 C5 C6 C7 176.00(18)
C2 C1 C6 C5 -0.4(3)
N2 C1 C6 C5 177.83(17)
C2 C1 C6 C7 -176.33(17)
N2 C1 C6 C7 1.9(2)
C16 O3 C7 C6 154.88(15)
C16 O3 C7 C17 22.33(18)
C16 O3 C7 C8 -95.85(16)
C5 C6 C7 O3 -67.2(2)
C1 C6 C7 O3 108.08(17)
C5 C6 C7 C17 53.9(3)
C1 C6 C7 C17 -130.82(18)
C5 C6 C7 C8 -178.44(19)
C1 C6 C7 C8 -3.20(18)
C1 N2 C8 O4 179.13(18)
C9 N2 C8 O4 -5.3(3)
C1 N2 C8 C7 -2.6(2)
C9 N2 C8 C7 173.02(17)
O3 C7 C8 O4 66.8(2)
C6 C7 C8 O4 -178.18(18)
C17 C7 C8 O4 -44.3(2)
O3 C7 C8 N2 -111.55(16)
C6 C7 C8 N2 3.52(18)
C17 C7 C8 N2 137.35(16)
C8 N2 C9 C10 99.5(2)
C1 N2 C9 C10 -85.5(2)
N2 C9 C10 C11 -61.2(3)
N2 C9 C10 C15 121.1(2)
C15 C10 C11 C12 -1.1(4)
C9 C10 C11 C12 -178.7(2)
C10 C11 C12 C13 1.3(5)
C11 C12 C13 C14 -0.6(5)
C12 C13 C14 C15 -0.3(6)
C11 C10 C15 C14 0.1(4)
C9 C10 C15 C14 177.8(2)
C13 C14 C15 C10 0.6(5)
C17 N1 C16 O3 -8.1(2)
C17 N1 C16 S1 170.99(16)
C7 O3 C16 N1 -10.1(2)
C7 O3 C16 S1 170.65(14)
C16 N1 C17 C18 139.56(18)
C16 N1 C17 C21 -99.7(2)
C16 N1 C17 C7 21.0(2)
O3 C7 C17 N1 -24.57(17)
C6 C7 C17 N1 -149.13(17)
C8 C7 C17 N1 88.04(17)
O3 C7 C17 C18 -142.53(16)
C6 C7 C17 C18 92.9(2)
C8 C7 C17 C18 -29.9(2)
O3 C7 C17 C21 92.08(19)
C6 C7 C17 C21 -32.5(3)
C8 C7 C17 C21 -155.31(18)
C19 O2 C18 O1 3.4(4)
C19 O2 C18 C17 -174.3(2)
N1 C17 C18 O1 19.9(3)
C21 C17 C18 O1 -101.2(3)
C7 C17 C18 O1 130.2(3)
N1 C17 C18 O2 -162.40(17)
C21 C17 C18 O2 76.5(2)
C7 C17 C18 O2 -52.1(2)
C18 O2 C19 C20 171.5(3)
