#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:37:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180513 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/82/7218284.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_7218284
loop_
_publ_author_name
'Meng, Xiao'
'Chen, Hao'
'Xu, Shu'
'Ma, Yuguo'
_publ_section_title
;
 Metal-free 1,3-dipolar cycloaddition polymerization via prearrangement of
 azide and alkyne in the solid state
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              9983
_journal_paper_doi               10.1039/C4CE01690D
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H9 F4 N3 O4'
_chemical_formula_sum            'C18 H9 F4 N3 O4'
_chemical_formula_weight         407.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                61.83(3)
_cell_angle_beta                 86.14(3)
_cell_angle_gamma                76.85(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1325(14)
_cell_length_b                   11.657(2)
_cell_length_c                   11.979(2)
_cell_measurement_reflns_used    2703
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4294
_cell_measurement_theta_min      1.9305
_cell_volume                     854.0(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_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  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6665
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.1067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1458P)²+0.6436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2711
_refine_ls_wR_factor_ref         0.2900
_reflns_number_gt                2370
_reflns_number_total             2983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01690d2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7218284--7218287.cif.'
_cod_original_cell_volume        854.1(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218284
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
F4 F 1.1851(3) -0.0849(2) 0.5887(2) 0.0465(7) Uani 1 1 d .
F2 F 0.8129(3) 0.0931(2) 0.9060(2) 0.0453(7) Uani 1 1 d .
F3 F 1.0863(4) 0.1747(2) 0.5094(2) 0.0463(7) Uani 1 1 d .
O3 O 0.7174(5) 0.6237(3) 0.7846(3) 0.0541(9) Uani 1 1 d .
F1 F 0.9215(4) -0.1664(2) 0.9852(2) 0.0478(7) Uani 1 1 d .
C5 C 1.0377(6) 0.0947(4) 0.6276(4) 0.0373(9) Uani 1 1 d .
C11 C 0.5873(6) 0.8052(4) 0.8228(4) 0.0390(10) Uani 1 1 d .
C12 C 0.5037(6) 0.8546(4) 0.9033(4) 0.0417(10) Uani 1 1 d .
H12 H 0.4900 0.7948 0.9897 0.050 Uiso 1 1 calc R
C3 C 0.9079(6) 0.0544(4) 0.8254(4) 0.0379(9) Uani 1 1 d .
O2 O 0.8709(5) 0.3297(3) 0.7443(3) 0.0481(8) Uani 1 1 d .
N3 N 1.1046(6) -0.2738(4) 0.8434(4) 0.0487(10) Uani 1 1 d .
C6 C 1.0933(6) -0.0417(4) 0.6686(4) 0.0361(9) Uani 1 1 d .
C14 C 0.4631(6) 1.0810(4) 0.7322(4) 0.0394(10) Uani 1 1 d .
C10 C 0.6606(7) 0.6585(4) 0.8743(4) 0.0460(11) Uani 1 1 d .
C4 C 0.9454(6) 0.1471(4) 0.7038(4) 0.0369(9) Uani 1 1 d .
C13 C 0.4392(6) 0.9919(4) 0.8586(4) 0.0386(10) Uani 1 1 d .
H13 H 0.3790 1.0249 0.9141 0.046 Uiso 1 1 calc R
O4 O 0.6670(6) 0.5799(3) 0.9865(3) 0.0630(10) Uani 1 1 d .
C1 C 1.0563(6) -0.1335(4) 0.7903(4) 0.0367(9) Uani 1 1 d .
C15 C 0.5461(6) 1.0298(4) 0.6509(4) 0.0409(10) Uani 1 1 d .
H15 H 0.5605 1.0892 0.5645 0.049 Uiso 1 1 calc R
C16 C 0.6076(6) 0.8933(4) 0.6951(4) 0.0421(10) Uani 1 1 d .
H16 H 0.6633 0.8595 0.6392 0.051 Uiso 1 1 calc R
O1 O 0.8511(5) 0.3724(3) 0.5430(3) 0.0569(9) Uani 1 1 d .
C17 C 0.4056(7) 1.2216(4) 0.6874(4) 0.0464(11) Uani 1 1 d .
C2 C 0.9635(6) -0.0813(4) 0.8668(4) 0.0379(9) Uani 1 1 d .
C7 C 0.8838(6) 0.2955(4) 0.6526(4) 0.0427(10) Uani 1 1 d .
N2 N 1.1840(6) -0.3246(4) 0.7769(4) 0.0544(10) Uani 1 1 d .
C8 C 0.8072(8) 0.4715(4) 0.7052(5) 0.0546(12) Uani 1 1 d .
H8A H 0.6828 0.5086 0.6558 0.066 Uiso 1 1 calc R
H8B H 0.9037 0.5205 0.6524 0.066 Uiso 1 1 calc R
C9 C 0.7855(8) 0.4825(5) 0.8252(5) 0.0567(13) Uani 1 1 d .
H9A H 0.6912 0.4319 0.8791 0.068 Uiso 1 1 calc R
H9B H 0.9105 0.4477 0.8737 0.068 Uiso 1 1 calc R
C18 C 0.3560(8) 1.3380(5) 0.6502(5) 0.0625(14) Uani 1 1 d .
H18 H 0.3162 1.4315 0.6203 0.075 Uiso 1 1 calc R
N1 N 1.2557(8) -0.3895(5) 0.7334(5) 0.0770(15) 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
C10 O3 C9 116.8(4)
F3 C5 C4 121.2(4)
F3 C5 C6 116.2(4)
C4 C5 C6 122.5(4)
C12 C11 C16 119.9(4)
C12 C11 C10 119.2(4)
C16 C11 C10 120.8(4)
C11 C12 C13 120.4(4)
C11 C12 H12 119.8
C13 C12 H12 119.8
F2 C3 C2 116.8(4)
F2 C3 C4 121.5(4)
C2 C3 C4 121.7(4)
C7 O2 C8 116.1(3)
N2 N3 C1 118.8(4)
F4 C6 C5 118.9(3)
F4 C6 C1 120.0(4)
C5 C6 C1 121.2(4)
C13 C14 C15 118.9(4)
C13 C14 C17 120.5(4)
C15 C14 C17 120.6(4)
O4 C10 O3 124.1(4)
O4 C10 C11 123.2(4)
O3 C10 C11 112.7(4)
C5 C4 C3 116.0(4)
C5 C4 C7 120.0(4)
C3 C4 C7 123.9(4)
C12 C13 C14 120.2(4)
C12 C13 H13 119.9
C14 C13 H13 119.9
C2 C1 C6 116.4(4)
C2 C1 N3 116.8(4)
C6 C1 N3 126.8(4)
C16 C15 C14 120.8(4)
C16 C15 H15 119.6
C14 C15 H15 119.6
C15 C16 C11 119.7(4)
C15 C16 H16 120.1
C11 C16 H16 120.1
C18 C17 C14 179.3(5)
F1 C2 C3 119.1(4)
F1 C2 C1 118.7(4)
C3 C2 C1 122.2(4)
O1 C7 O2 124.6(4)
O1 C7 C4 123.8(4)
O2 C7 C4 111.7(4)
N1 N2 N3 168.9(5)
O2 C8 C9 105.8(4)
O2 C8 H8A 110.6
C9 C8 H8A 110.6
O2 C8 H8B 110.6
C9 C8 H8B 110.6
H8A C8 H8B 108.7
O3 C9 C8 105.0(4)
O3 C9 H9A 110.7
C8 C9 H9A 110.7
O3 C9 H9B 110.7
C8 C9 H9B 110.7
H9A C9 H9B 108.8
C17 C18 H18 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F4 C6 1.350(4)
F2 C3 1.334(4)
F3 C5 1.352(4)
O3 C10 1.326(5)
O3 C9 1.448(5)
F1 C2 1.355(5)
C5 C4 1.379(6)
C5 C6 1.389(6)
C11 C12 1.382(6)
C11 C16 1.404(6)
C11 C10 1.489(6)
C12 C13 1.396(6)
C12 H12 0.9500
C3 C2 1.381(6)
C3 C4 1.397(6)
O2 C7 1.325(5)
O2 C8 1.454(5)
N3 N2 1.240(5)
N3 C1 1.410(5)
C6 C1 1.394(6)
C14 C13 1.401(6)
C14 C15 1.402(6)
C14 C17 1.427(6)
C10 O4 1.215(6)
C4 C7 1.501(6)
C13 H13 0.9500
C1 C2 1.382(6)
C15 C16 1.387(6)
C15 H15 0.9500
C16 H16 0.9500
O1 C7 1.191(5)
C17 C18 1.182(7)
N2 N1 1.125(6)
C8 C9 1.497(7)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C18 H18 0.9500
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
C16 C11 C12 C13 0.0(6)
C10 C11 C12 C13 178.0(4)
F3 C5 C6 F4 -1.9(5)
C4 C5 C6 F4 -179.2(3)
F3 C5 C6 C1 177.9(3)
C4 C5 C6 C1 0.6(6)
C9 O3 C10 O4 1.8(7)
C9 O3 C10 C11 -178.1(4)
C12 C11 C10 O4 -6.9(7)
C16 C11 C10 O4 171.0(4)
C12 C11 C10 O3 173.0(4)
C16 C11 C10 O3 -9.0(6)
F3 C5 C4 C3 -178.1(3)
C6 C5 C4 C3 -0.9(6)
F3 C5 C4 C7 4.6(6)
C6 C5 C4 C7 -178.2(4)
F2 C3 C4 C5 -177.4(3)
C2 C3 C4 C5 1.1(6)
F2 C3 C4 C7 -0.2(6)
C2 C3 C4 C7 178.3(4)
C11 C12 C13 C14 -1.6(6)
C15 C14 C13 C12 2.3(6)
C17 C14 C13 C12 -177.1(4)
F4 C6 C1 C2 179.3(3)
C5 C6 C1 C2 -0.5(6)
F4 C6 C1 N3 -0.3(6)
C5 C6 C1 N3 179.9(4)
N2 N3 C1 C2 178.4(4)
N2 N3 C1 C6 -2.0(7)
C13 C14 C15 C16 -1.4(6)
C17 C14 C15 C16 178.0(4)
C14 C15 C16 C11 -0.2(6)
C12 C11 C16 C15 1.0(6)
C10 C11 C16 C15 -177.0(4)
C13 C14 C17 C18 -79(42)
C15 C14 C17 C18 102(42)
F2 C3 C2 F1 -0.7(6)
C4 C3 C2 F1 -179.3(3)
F2 C3 C2 C1 177.5(3)
C4 C3 C2 C1 -1.1(6)
C6 C1 C2 F1 179.0(3)
N3 C1 C2 F1 -1.4(5)
C6 C1 C2 C3 0.7(6)
N3 C1 C2 C3 -179.6(4)
C8 O2 C7 O1 1.7(7)
C8 O2 C7 C4 -178.5(4)
C5 C4 C7 O1 25.1(7)
C3 C4 C7 O1 -152.0(5)
C5 C4 C7 O2 -154.8(4)
C3 C4 C7 O2 28.2(6)
C1 N3 N2 N1 180(3)
C7 O2 C8 C9 174.4(4)
C10 O3 C9 C8 170.8(4)
O2 C8 C9 O3 -178.6(4)
