#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/22/7222294.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_7222294
loop_
_publ_author_name
'sun, kai'
'Ma, Fengji'
'Liu, Lulu'
'Sun, Jingjing'
'Liu, Xin'
'Wang, Yachao'
'Zhang, Zhiguo'
'Zhang, Guisheng'
_publ_section_title
;
 Iodine-Mediated Regioselective C--N and C--I Bonds Formation of Alkenes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA14407H
_journal_year                    2015
_chemical_formula_sum            'C14 H12 I N3 O0'
_chemical_formula_weight         349.17
_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
_audit_update_record
;
2015-09-03 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.24(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7065(17)
_cell_length_b                   13.352(3)
_cell_length_c                   11.519(2)
_cell_measurement_reflns_used    4398
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.35
_cell_volume                     1321.7(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      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4771
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.408
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.676
_refine_diff_density_min         -1.418
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2139
_reflns_number_total             2315
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c5ra14407h2.cif
_cod_data_source_block           1
_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/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 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7222294
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
I1 I 0.71217(3) 0.072424(18) 0.78272(2) 0.02315(18) Uani 1 1 d .
N1 N 0.9148(3) 0.2868(2) 0.8121(3) 0.0180(6) Uani 1 1 d .
N2 N 0.9108(3) 0.2858(2) 0.6932(3) 0.0208(7) Uani 1 1 d .
C4 C 1.4114(4) 0.2853(3) 0.8933(3) 0.0261(9) Uani 1 1 d .
H4A H 1.4710 0.3253 0.8517 0.031 Uiso 1 1 calc R
C14 C 0.8402(4) 0.3702(3) 0.8435(3) 0.0165(7) Uani 1 1 d .
C2 C 1.3922(4) 0.1786(3) 1.0543(3) 0.0245(8) Uani 1 1 d .
H2A H 1.4406 0.1445 1.1206 0.029 Uiso 1 1 calc R
C1 C 1.2364(4) 0.1725(3) 1.0242(3) 0.0225(8) Uani 1 1 d .
H1A H 1.1788 0.1359 1.0707 0.027 Uiso 1 1 calc R
C7 C 0.9859(4) 0.2064(3) 0.8875(3) 0.0189(7) Uani 1 1 d .
H7A H 0.9388 0.2062 0.9593 0.023 Uiso 1 1 calc R
C11 C 0.6856(5) 0.5483(3) 0.8419(4) 0.0272(9) Uani 1 1 d .
H11A H 0.6361 0.6098 0.8442 0.033 Uiso 1 1 calc R
C10 C 0.7093(4) 0.5107(3) 0.7346(4) 0.0223(8) Uani 1 1 d .
H10A H 0.6740 0.5440 0.6645 0.027 Uiso 1 1 calc R
C8 C 0.9569(4) 0.1053(3) 0.8291(3) 0.0213(8) Uani 1 1 d .
H8A H 1.0058 0.0539 0.8819 0.026 Uiso 1 1 calc R
H8B H 1.0047 0.1038 0.7586 0.026 Uiso 1 1 calc R
C6 C 1.1604(4) 0.2213(3) 0.9226(3) 0.0181(7) Uani 1 1 d .
C12 C 0.7335(4) 0.4970(3) 0.9472(4) 0.0277(9) Uani 1 1 d .
H12A H 0.7105 0.5244 1.0166 0.033 Uiso 1 1 calc R
C13 C 0.8138(5) 0.4070(3) 0.9528(4) 0.0224(8) Uani 1 1 d .
H13A H 0.8475 0.3738 1.0232 0.027 Uiso 1 1 calc R
C5 C 1.2491(4) 0.2779(3) 0.8567(3) 0.0246(8) Uani 1 1 d .
H5A H 1.2019 0.3106 0.7890 0.029 Uiso 1 1 calc R
N3 N 0.8364(3) 0.3648(3) 0.6466(3) 0.0224(7) Uani 1 1 d .
C3 C 1.4808(4) 0.2335(3) 0.9902(3) 0.0239(8) Uani 1 1 d .
H3A H 1.5882 0.2357 1.0122 0.029 Uiso 1 1 calc R
C9 C 0.7900(4) 0.4187(3) 0.7369(4) 0.0178(9) Uani 1 1 d .
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'
I I -0.4742 1.8119 '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
N2 N1 C14 109.7(3)
N2 N1 C7 122.1(3)
C14 N1 C7 128.1(3)
N3 N2 N1 109.5(3)
C3 C4 C5 119.8(4)
C3 C4 H4A 120.1
C5 C4 H4A 120.1
N1 C14 C9 103.9(3)
N1 C14 C13 132.5(4)
C9 C14 C13 123.6(4)
C1 C2 C3 121.7(4)
C1 C2 H2A 119.1
C3 C2 H2A 119.1
C2 C1 C6 120.4(4)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
N1 C7 C8 111.6(3)
N1 C7 C6 111.9(3)
C8 C7 C6 108.8(3)
N1 C7 H7A 108.1
C8 C7 H7A 108.1
C6 C7 H7A 108.1
C10 C11 C12 122.2(4)
C10 C11 H11A 118.9
C12 C11 H11A 118.9
C11 C10 C9 116.4(4)
C11 C10 H10A 121.8
C9 C10 H10A 121.8
C7 C8 I1 112.3(2)
C7 C8 H8A 109.1
I1 C8 H8A 109.1
C7 C8 H8B 109.1
I1 C8 H8B 109.1
H8A C8 H8B 107.9
C5 C6 C1 118.5(3)
C5 C6 C7 123.0(3)
C1 C6 C7 118.5(3)
C13 C12 C11 122.9(4)
C13 C12 H12A 118.5
C11 C12 H12A 118.5
C12 C13 C14 114.6(4)
C12 C13 H13A 122.7
C14 C13 H13A 122.7
C6 C5 C4 119.5(4)
C6 C5 H5A 120.3
C4 C5 H5A 120.3
N2 N3 C9 107.3(3)
C2 C3 C4 120.0(3)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
N3 C9 C14 109.5(3)
N3 C9 C10 130.1(4)
C14 C9 C10 120.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C8 2.157(4)
N1 N2 1.364(4)
N1 C14 1.367(5)
N1 C7 1.455(5)
N2 N3 1.308(4)
C4 C3 1.368(5)
C4 C5 1.412(5)
C4 H4A 0.9300
C14 C9 1.395(6)
C14 C13 1.404(5)
C2 C1 1.348(5)
C2 C3 1.364(5)
C2 H2A 0.9300
C1 C6 1.408(5)
C1 H1A 0.9300
C7 C8 1.512(5)
C7 C6 1.522(5)
C7 H7A 0.9800
C11 C10 1.381(6)
C11 C12 1.397(6)
C11 H11A 0.9300
C10 C9 1.413(5)
C10 H10A 0.9300
C8 H8A 0.9700
C8 H8B 0.9700
C6 C5 1.390(5)
C12 C13 1.386(6)
C12 H12A 0.9300
C13 H13A 0.9300
C5 H5A 0.9300
N3 C9 1.377(5)
C3 H3A 0.9300
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
C14 N1 N2 N3 -0.2(4)
C7 N1 N2 N3 178.0(3)
N2 N1 C14 C9 0.5(4)
C7 N1 C14 C9 -177.6(3)
N2 N1 C14 C13 -178.9(4)
C7 N1 C14 C13 3.0(6)
C3 C2 C1 C6 1.6(6)
N2 N1 C7 C8 -37.2(4)
C14 N1 C7 C8 140.7(3)
N2 N1 C7 C6 85.1(4)
C14 N1 C7 C6 -97.0(4)
C12 C11 C10 C9 -2.3(6)
N1 C7 C8 I1 -58.8(3)
C6 C7 C8 I1 177.2(2)
C2 C1 C6 C5 -1.9(5)
C2 C1 C6 C7 175.8(3)
N1 C7 C6 C5 -24.1(5)
C8 C7 C6 C5 99.7(4)
N1 C7 C6 C1 158.3(3)
C8 C7 C6 C1 -77.9(4)
C10 C11 C12 C13 2.8(6)
C11 C12 C13 C14 -1.4(6)
N1 C14 C13 C12 179.0(4)
C9 C14 C13 C12 -0.3(5)
C1 C6 C5 C4 -0.3(5)
C7 C6 C5 C4 -177.9(3)
C3 C4 C5 C6 2.8(6)
N1 N2 N3 C9 -0.2(4)
C1 C2 C3 C4 0.9(6)
C5 C4 C3 C2 -3.1(6)
N2 N3 C9 C14 0.5(4)
N2 N3 C9 C10 178.5(4)
N1 C14 C9 N3 -0.6(4)
C13 C14 C9 N3 178.9(3)
N1 C14 C9 C10 -178.8(3)
C13 C14 C9 C10 0.7(5)
C11 C10 C9 N3 -177.2(4)
C11 C10 C9 C14 0.6(5)
