#------------------------------------------------------------------------------
#$Date: 2017-06-20 07:07:34 +0300 (Tue, 20 Jun 2017) $
#$Revision: 197960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/57/7155710.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_7155710
loop_
_publ_author_name
'Ji, Heng'
'Ni, Hui-qiong'
'Zhi, Peng'
'Xi, Zi-wei'
'Wang, Wei'
'Shi, Jian-jun'
'Shen, Yong-miao'
_publ_section_title
;
 Visible-light mediated directed perfluoroalkylation of hydrazones
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01144J
_journal_year                    2017
_chemical_formula_moiety         'C13 H12 F3 N3 O'
_chemical_formula_sum            'C13 H12 F3 N3 O'
_chemical_formula_weight         283.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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
_audit_update_record
;
2017-05-05 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.751(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2713(11)
_cell_length_b                   15.4059(17)
_cell_length_c                   10.6562(14)
_cell_measurement_reflns_used    1385
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.83
_cell_volume                     1334.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6804
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0528
_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)+(0.0438P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1515
_reflns_number_total             2415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01144j2.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
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 2yn  '
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7155710
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
C1 C 0.8311(3) 0.27309(15) 0.9619(2) 0.0203(6) Uani 1 1 d .
C2 C 0.6796(3) 0.24077(15) 0.9004(2) 0.0235(6) Uani 1 1 d .
H2 H 0.6749 0.2023 0.8302 0.028 Uiso 1 1 calc R
C3 C 0.5364(3) 0.26412(16) 0.9405(2) 0.0263(6) Uani 1 1 d .
H3 H 0.4334 0.2422 0.8978 0.032 Uiso 1 1 calc R
C4 C 0.5444(3) 0.32002(15) 1.0441(2) 0.0243(6) Uani 1 1 d .
C5 C 0.6955(3) 0.35197(16) 1.1076(2) 0.0261(6) Uani 1 1 d .
H5 H 0.7003 0.3900 1.1784 0.031 Uiso 1 1 calc R
C6 C 0.8378(3) 0.32780(16) 1.0667(2) 0.0243(6) Uani 1 1 d .
H6 H 0.9411 0.3487 1.1105 0.029 Uiso 1 1 calc R
C7 C 0.9868(3) 0.24429(14) 0.9207(2) 0.0193(6) Uani 1 1 d .
C8 C 1.1547(3) 0.45064(16) 0.6367(3) 0.0314(7) Uani 1 1 d .
H8A H 1.2576 0.4730 0.6138 0.038 Uiso 1 1 calc R
H8B H 1.0878 0.4243 0.5593 0.038 Uiso 1 1 calc R
C9 C 1.1955(3) 0.38259(16) 0.7391(3) 0.0298(7) Uani 1 1 d .
H9A H 1.2537 0.3337 0.7068 0.036 Uiso 1 1 calc R
H9B H 1.2695 0.4077 0.8141 0.036 Uiso 1 1 calc R
C10 C 0.9397(3) 0.42049(15) 0.8113(2) 0.0247(6) Uani 1 1 d .
H10A H 0.9922 0.4475 0.8931 0.030 Uiso 1 1 calc R
H10B H 0.8321 0.3964 0.8218 0.030 Uiso 1 1 calc R
C11 C 0.9147(3) 0.48809(15) 0.7059(2) 0.0279(6) Uani 1 1 d .
H11A H 0.8507 0.4620 0.6272 0.033 Uiso 1 1 calc R
H11B H 0.8497 0.5369 0.7311 0.033 Uiso 1 1 calc R
C12 C 1.0501(3) 0.15818(17) 0.9761(3) 0.0290(6) Uani 1 1 d .
C13 C 0.3953(4) 0.34495(19) 1.0864(2) 0.0330(7) Uani 1 1 d .
F1 F 1.1945(2) 0.13566(10) 0.94963(16) 0.0482(5) Uani 1 1 d .
F2 F 1.0660(2) 0.15715(11) 1.10325(15) 0.0562(6) Uani 1 1 d .
F3 F 0.9463(2) 0.09316(10) 0.93532(18) 0.0594(6) Uani 1 1 d .
N1 N 1.0758(2) 0.27676(12) 0.84648(18) 0.0210(5) Uani 1 1 d .
N2 N 1.0453(2) 0.35058(12) 0.77763(19) 0.0231(5) Uani 1 1 d .
N3 N 0.2763(3) 0.36568(18) 1.1187(2) 0.0495(7) Uani 1 1 d .
O1 O 1.0655(2) 0.52081(10) 0.67942(16) 0.0291(5) 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'
F F 0.0171 0.0103 '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
C6 C1 C2 119.4(2)
C6 C1 C7 120.4(2)
C2 C1 C7 120.1(2)
C3 C2 C1 120.6(2)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 119.4(2)
C2 C3 H3 120.3
C4 C3 H3 120.3
C3 C4 C5 120.6(2)
C3 C4 C13 119.8(2)
C5 C4 C13 119.7(2)
C6 C5 C4 119.4(2)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C6 C1 120.5(2)
C5 C6 H6 119.7
C1 C6 H6 119.7
N1 C7 C1 133.5(2)
N1 C7 C12 112.9(2)
C1 C7 C12 113.5(2)
O1 C8 C9 110.7(2)
O1 C8 H8A 109.5
C9 C8 H8A 109.5
O1 C8 H8B 109.5
C9 C8 H8B 109.5
H8A C8 H8B 108.1
N2 C9 C8 110.5(2)
N2 C9 H9A 109.5
C8 C9 H9A 109.5
N2 C9 H9B 109.5
C8 C9 H9B 109.5
H9A C9 H9B 108.1
N2 C10 C11 109.1(2)
N2 C10 H10A 109.9
C11 C10 H10A 109.9
N2 C10 H10B 109.9
C11 C10 H10B 109.9
H10A C10 H10B 108.3
O1 C11 C10 112.8(2)
O1 C11 H11A 109.0
C10 C11 H11A 109.0
O1 C11 H11B 109.0
C10 C11 H11B 109.0
H11A C11 H11B 107.8
F1 C12 F2 106.9(2)
F1 C12 F3 106.5(2)
F2 C12 F3 104.9(2)
F1 C12 C7 114.1(2)
F2 C12 C7 111.7(2)
F3 C12 C7 112.1(2)
N3 C13 C4 179.0(3)
C7 N1 N2 126.5(2)
N1 N2 C9 110.69(18)
N1 N2 C10 122.85(19)
C9 N2 C10 113.23(19)
C11 O1 C8 108.60(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.392(3)
C1 C2 1.393(3)
C1 C7 1.503(3)
C2 C3 1.380(4)
C2 H2 0.9500
C3 C4 1.392(3)
C3 H3 0.9500
C4 C5 1.395(3)
C4 C13 1.441(4)
C5 C6 1.381(3)
C5 H5 0.9500
C6 H6 0.9500
C7 N1 1.278(3)
C7 C12 1.506(3)
C8 O1 1.430(3)
C8 C9 1.506(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 N2 1.464(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 N2 1.472(3)
C10 C11 1.517(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 O1 1.422(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 F1 1.324(3)
C12 F2 1.336(3)
C12 F3 1.338(3)
C13 N3 1.147(3)
N1 N2 1.351(3)
