#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:06:08 +0100 (Fri 08 de Nov de 2019) $
#$Revision: 225292 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/70/7157064.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_7157064
loop_
_publ_author_name
'Liu, Shulin'
'Wang, Rui'
'Zhu, Bo'
'Guan, Wei'
'Liang, Fushun'
_publ_section_title
;
 Photo- and dioxygen-enabled radical C(sp³)-N(sp²)
 cross-coupling between guanidines and perfluoroalkyl iodides.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8695
_journal_page_last               8700
_journal_paper_doi               10.1039/c9ob01520e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C9 H12 F7 N3 O'
_chemical_formula_sum            'C9 H12 F7 N3 O'
_chemical_formula_weight         311.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-04-04 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.506(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7613(10)
_cell_length_b                   7.2600(4)
_cell_length_c                   15.9064(13)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      3.10
_cell_volume                     1330.91(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.58
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12981
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.743
_diffrn_reflns_theta_min         2.398
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.13(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.566
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.566
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.1231
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3689
_refine_ls_wR_factor_ref         0.4095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1684
_reflns_number_total             2523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob01520e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7157064--7157065.cif.'
_cod_database_code               7157064
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.7550(5) 0.6486(4) 0.5024(2) 0.1221(19) Uani 1 1 d .
F2 F 0.6117(3) 0.4849(6) 0.4418(3) 0.1083(16) Uani 1 1 d .
F3 F 0.9013(4) 0.3881(9) 0.4455(4) 0.159(2) Uani 1 1 d .
F4 F 0.7469(6) 0.2649(6) 0.3742(3) 0.156(3) Uani 1 1 d .
F5 F 0.8443(7) 0.4970(11) 0.2810(4) 0.188(3) Uani 1 1 d .
F6 F 0.8342(9) 0.7116(9) 0.3621(4) 0.218(4) Uani 1 1 d .
F7 F 0.6855(6) 0.5920(10) 0.2965(4) 0.185(3) Uani 1 1 d .
C1 C 0.8470(5) -0.1148(7) 0.7102(4) 0.0803(17) Uani 1 1 d .
H1A H 0.9252 -0.1589 0.7165 0.120 Uiso 1 1 calc R
H1B H 0.8422 -0.0303 0.7558 0.120 Uiso 1 1 calc R
H1C H 0.7958 -0.2169 0.7124 0.120 Uiso 1 1 calc R
C2 C 0.9020(5) 0.0089(8) 0.5784(5) 0.0858(19) Uani 1 1 d .
H2A H 0.9720 -0.0534 0.6049 0.129 Uiso 1 1 calc R
H2B H 0.8757 -0.0382 0.5215 0.129 Uiso 1 1 calc R
H2C H 0.9169 0.1385 0.5757 0.129 Uiso 1 1 calc R
C3 C 0.6036(5) -0.1974(7) 0.6569(4) 0.0807(17) Uani 1 1 d .
H3A H 0.5305 -0.2105 0.6743 0.121 Uiso 1 1 calc R
H3B H 0.6065 -0.2798 0.6101 0.121 Uiso 1 1 calc R
H3C H 0.6654 -0.2264 0.7043 0.121 Uiso 1 1 calc R
C4 C 0.5093(5) 0.1033(9) 0.6157(4) 0.0774(16) Uani 1 1 d .
H4A H 0.4518 0.0390 0.6395 0.116 Uiso 1 1 calc R
H4B H 0.5247 0.2207 0.6434 0.116 Uiso 1 1 calc R
H4C H 0.4813 0.1214 0.5553 0.116 Uiso 1 1 calc R
C5 C 0.7076(4) 0.0551(5) 0.6017(3) 0.0481(11) Uani 1 1 d .
C6 C 0.7471(4) 0.3470(6) 0.5578(3) 0.0549(12) Uani 1 1 d .
C7 C 0.7266(5) 0.4752(6) 0.4783(3) 0.0641(14) Uani 1 1 d .
C8 C 0.7895(6) 0.4253(8) 0.4095(4) 0.0784(16) Uani 1 1 d .
C9 C 0.7915(8) 0.5567(11) 0.3355(5) 0.100(2) Uani 1 1 d .
N1 N 0.8135(3) -0.0219(5) 0.6286(3) 0.0588(11) Uani 1 1 d .
N2 N 0.6168(3) -0.0058(5) 0.6291(2) 0.0581(11) Uani 1 1 d .
N3 N 0.6920(3) 0.1914(5) 0.5417(2) 0.0565(11) Uani 1 1 d .
O1 O 0.8076(4) 0.4070(5) 0.6233(2) 0.0850(14) 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
N1 C5 N3 120.5(4)
N2 C5 N1 121.1(4)
N2 C5 N3 118.3(4)
N3 C6 C7 111.7(4)
O1 C6 C7 116.9(4)
O1 C6 N3 131.3(4)
F1 C7 F2 104.1(4)
F1 C7 C6 110.0(4)
F1 C7 C8 108.0(4)
F2 C7 C6 111.0(4)
F2 C7 C8 107.2(5)
C8 C7 C6 115.9(4)
F3 C8 C7 108.8(5)
F3 C8 C9 106.8(6)
F4 C8 F3 104.7(6)
F4 C8 C7 108.7(5)
F4 C8 C9 106.4(5)
C7 C8 C9 120.4(5)
F5 C9 F6 108.8(8)
F5 C9 F7 107.5(8)
F5 C9 C8 114.1(7)
F6 C9 F7 105.2(9)
F6 C9 C8 111.4(7)
F7 C9 C8 109.3(6)
C1 N1 C2 118.0(5)
C5 N1 C1 123.0(4)
C5 N1 C2 118.6(4)
C4 N2 C3 114.4(5)
C5 N2 C3 124.0(4)
C5 N2 C4 120.3(4)
C6 N3 C5 120.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.338(5)
F2 C7 1.362(6)
F3 C8 1.353(7)
F4 C8 1.346(7)
F5 C9 1.240(9)
F6 C9 1.269(9)
F7 C9 1.302(10)
C1 N1 1.445(7)
C2 N1 1.450(7)
C3 N2 1.476(6)
C4 N2 1.471(6)
C5 N1 1.354(5)
C5 N2 1.308(5)
C5 N3 1.362(5)
C6 C7 1.549(7)
C6 N3 1.302(5)
C6 O1 1.219(6)
C7 C8 1.483(8)
C8 C9 1.518(9)
