#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:25:13 +0200 (Mon 05 de Jun de 2023) $
#$Revision: 284266 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/65/7246586.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_7246586
loop_
_publ_author_name
'Meng, Xiao'
'Xu, Shu'
'Chen, Changqing'
'Guo, Lihui'
'Ma, Yuguo'
_publ_section_title
;
 Topochemical 1,3-dipolar cycloaddition polymerization assisted by
 non-covalent interactions
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              2706
_journal_page_last               2711
_journal_paper_doi               10.1039/D3CE00105A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C19 H12 F4 N4 O3'
_chemical_formula_sum            'C19 H12 F4 N4 O3'
_chemical_formula_weight         420.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2016-01-21 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.46(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.925(3)
_cell_length_b                   27.776(11)
_cell_length_c                   9.963(5)
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4814
_cell_measurement_theta_min      1.4663
_cell_volume                     1837.8(14)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0213
_diffrn_orient_matrix_UB_12      0.1376
_diffrn_orient_matrix_UB_13      0.0572
_diffrn_orient_matrix_UB_21      0.0356
_diffrn_orient_matrix_UB_22      -0.0052
_diffrn_orient_matrix_UB_23      -0.0007
_diffrn_orient_matrix_UB_31      0.0079
_diffrn_orient_matrix_UB_32      0.0651
_diffrn_orient_matrix_UB_33      -0.0815
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14246
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.197
_diffrn_reflns_theta_min         1.466
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow''
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0869
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0838P)²+1.6573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2795
_reflns_number_total             3293
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00105a2.cif
_cod_data_source_block           sa3436
_cod_depositor_comments          'Adding full bibliography for 7246586.cif.'
_cod_database_code               7246586
_shelxl_version_number           2013-4
_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.
;
_diffrn_number_total             4254
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17)
2.c :
 C19(H19)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2742(5) 0.49756(9) 0.9483(3) 0.0803(8) Uani 1 1 d . . . . .
F2 F 0.3986(5) 0.56794(10) 1.1317(3) 0.0799(8) Uani 1 1 d . . . . .
F3 F 0.3618(4) 0.67633(9) 0.7591(3) 0.0736(8) Uani 1 1 d . . . . .
F4 F 0.2458(4) 0.60520(10) 0.5785(3) 0.0771(8) Uani 1 1 d . . . . .
O1 O 0.5466(5) 0.70092(12) 1.0310(4) 0.0816(10) Uani 1 1 d . . . . .
O2 O 0.3741(4) 0.66347(10) 1.1594(3) 0.0616(8) Uani 1 1 d . . . . .
O3 O 0.0133(5) 0.75769(11) 1.4939(3) 0.0652(8) Uani 1 1 d . . . . .
N1 N 0.1307(10) 0.43325(19) 0.6875(7) 0.127(2) Uani 1 1 d . . . . .
N2 N 0.1642(7) 0.47323(19) 0.6804(5) 0.0844(13) Uani 1 1 d . . . . .
N3 N 0.1909(6) 0.51590(16) 0.6489(4) 0.0731(11) Uani 1 1 d . . . . .
N4 N 0.0047(5) 0.73299(12) 1.2789(3) 0.0471(8) Uani 1 1 d . . . . .
C1 C 0.2580(6) 0.54920(15) 0.7572(4) 0.0562(10) Uani 1 1 d . . . . .
C2 C 0.2966(6) 0.54198(14) 0.9004(5) 0.0574(10) Uani 1 1 d . . . . .
C3 C 0.3602(6) 0.57925(16) 0.9943(4) 0.0569(10) Uani 1 1 d . . . . .
C4 C 0.3849(6) 0.62565(14) 0.9534(4) 0.0526(10) Uani 1 1 d . . . . .
C5 C 0.3453(6) 0.63199(15) 0.8113(4) 0.0531(10) Uani 1 1 d . . . . .
C6 C 0.2843(6) 0.59573(15) 0.7160(4) 0.0530(10) Uani 1 1 d . . . . .
C7 C 0.4476(6) 0.66750(16) 1.0522(5) 0.0610(11) Uani 1 1 d . . . . .
C8 C 0.4190(7) 0.70276(16) 1.2601(5) 0.0625(11) Uani 1 1 d . . . . .
H8A H 0.3631 0.7327 1.2155 0.075 Uiso 1 1 calc R . . . .
H8B H 0.5635 0.7066 1.2981 0.075 Uiso 1 1 calc R . . . .
C9 C 0.3260(6) 0.69012(16) 1.3744(4) 0.0602(11) Uani 1 1 d . . . . .
H9A H 0.3653 0.7142 1.4477 0.072 Uiso 1 1 calc R . . . .
H9B H 0.3799 0.6594 1.4145 0.072 Uiso 1 1 calc R . . . .
C10 C 0.0979(6) 0.68683(15) 1.3273(4) 0.0530(10) Uani 1 1 d . . . . .
H10A H 0.0571 0.6635 1.2522 0.064 Uiso 1 1 calc R . . . .
H10B H 0.0507 0.6756 1.4046 0.064 Uiso 1 1 calc R . . . .
C11 C -0.0268(5) 0.76598(14) 1.3663(4) 0.0461(9) Uani 1 1 d . . . . .
C12 C -0.1061(5) 0.81415(14) 1.3103(3) 0.0433(8) Uani 1 1 d . . . . .
C13 C -0.1088(5) 0.85033(15) 1.4064(4) 0.0515(10) Uani 1 1 d . . . . .
H13 H -0.0720 0.8430 1.5013 0.062 Uiso 1 1 calc R . . . .
C14 C -0.1641(6) 0.89643(15) 1.3645(4) 0.0527(10) Uani 1 1 d . . . . .
H14 H -0.1645 0.9199 1.4309 0.063 Uiso 1 1 calc R . . . .
C15 C -0.2198(5) 0.90838(15) 1.2230(4) 0.0520(9) Uani 1 1 d . . . . .
C16 C -0.2227(6) 0.87195(15) 1.1253(4) 0.0546(10) Uani 1 1 d . . . . .
H16 H -0.2630 0.8793 1.0303 0.065 Uiso 1 1 calc R . . . .
C17 C -0.1672(5) 0.82550(14) 1.1671(4) 0.0493(9) Uani 1 1 d . . . . .
H17 H -0.1701 0.8017 1.1008 0.059 Uiso 1 1 calc R . . . .
C18 C -0.2737(6) 0.95699(18) 1.1777(4) 0.0609(11) Uani 1 1 d . . . . .
C19 C -0.3115(8) 0.99763(18) 1.1441(5) 0.0708(13) Uani 1 1 d . . . . .
H19 H -0.3411 1.0295 1.1177 0.085 Uiso 1 1 calc R . . . .
H4 H -0.014(6) 0.7392(14) 1.204(4) 0.044(11) Uiso 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 116.2(3) . . ?
N1 N2 N3 169.5(6) . . ?
N2 N3 C1 118.2(4) . . ?
C11 N4 C10 122.2(3) . . ?
C2 C1 N3 128.5(4) . . ?
C6 C1 N3 115.6(4) . . ?
C6 C1 C2 115.9(4) . . ?
F1 C2 C1 119.2(4) . . ?
F1 C2 C3 119.5(4) . . ?
C3 C2 C1 121.3(4) . . ?
F2 C3 C2 116.3(4) . . ?
F2 C3 C4 120.7(4) . . ?
C4 C3 C2 122.9(4) . . ?
C3 C4 C7 124.4(4) . . ?
C5 C4 C3 114.8(4) . . ?
C5 C4 C7 120.7(4) . . ?
F3 C5 C4 119.9(4) . . ?
F3 C5 C6 116.5(4) . . ?
C6 C5 C4 123.6(4) . . ?
F4 C6 C1 118.7(4) . . ?
F4 C6 C5 119.8(4) . . ?
C5 C6 C1 121.6(4) . . ?
O1 C7 O2 125.4(4) . . ?
O1 C7 C4 123.5(4) . . ?
O2 C7 C4 111.1(4) . . ?
O2 C8 C9 107.1(3) . . ?
C8 C9 C10 114.3(3) . . ?
N4 C10 C9 112.0(3) . . ?
O3 C11 N4 120.9(4) . . ?
O3 C11 C12 120.0(3) . . ?
N4 C11 C12 119.1(3) . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 C17 118.5(4) . . ?
C17 C12 C11 123.6(3) . . ?
C14 C13 C12 121.6(4) . . ?
C13 C14 C15 120.4(4) . . ?
C14 C15 C16 118.5(4) . . ?
C14 C15 C18 120.9(4) . . ?
C16 C15 C18 120.6(4) . . ?
C17 C16 C15 121.3(4) . . ?
C16 C17 C12 119.7(4) . . ?
C19 C18 C15 177.4(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.348(5) . ?
F2 C3 1.355(5) . ?
F3 C5 1.354(5) . ?
F4 C6 1.345(5) . ?
O1 C7 1.208(5) . ?
O2 C7 1.311(5) . ?
O2 C8 1.455(5) . ?
O3 C11 1.244(4) . ?
N1 N2 1.141(6) . ?
N2 N3 1.253(6) . ?
N3 C1 1.397(6) . ?
N4 C10 1.455(5) . ?
N4 C11 1.324(5) . ?
C1 C2 1.390(6) . ?
C1 C6 1.384(6) . ?
C2 C3 1.381(6) . ?
C3 C4 1.377(6) . ?
C4 C5 1.375(6) . ?
C4 C7 1.506(6) . ?
C5 C6 1.366(6) . ?
C8 C9 1.500(6) . ?
C9 C10 1.518(6) . ?
C11 C12 1.493(5) . ?
C12 C13 1.391(5) . ?
C12 C17 1.404(5) . ?
C13 C14 1.368(6) . ?
C14 C15 1.392(5) . ?
C15 C16 1.400(6) . ?
C15 C18 1.439(6) . ?
C16 C17 1.377(6) . ?
C18 C19 1.185(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O3 0.74(4) 2.16(4) 2.869(4) 162(4) 4_575
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 F2 0.7(6) . . . . ?
F1 C2 C3 C4 -179.4(4) . . . . ?
F2 C3 C4 C5 178.6(3) . . . . ?
F2 C3 C4 C7 -2.2(6) . . . . ?
F3 C5 C6 F4 0.5(5) . . . . ?
F3 C5 C6 C1 -178.5(3) . . . . ?
O2 C8 C9 C10 -64.1(5) . . . . ?
O3 C11 C12 C13 7.9(5) . . . . ?
O3 C11 C12 C17 -175.8(3) . . . . ?
N1 N2 N3 C1 179(3) . . . . ?
N2 N3 C1 C2 -1.7(7) . . . . ?
N2 N3 C1 C6 -179.9(4) . . . . ?
N3 C1 C2 F1 1.8(6) . . . . ?
N3 C1 C2 C3 -179.1(4) . . . . ?
N3 C1 C6 F4 -0.4(5) . . . . ?
N3 C1 C6 C5 178.6(4) . . . . ?
N4 C11 C12 C13 -170.4(3) . . . . ?
N4 C11 C12 C17 5.9(5) . . . . ?
C1 C2 C3 F2 -178.3(3) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C2 C1 C6 F4 -178.9(3) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C2 C3 C4 C7 178.0(4) . . . . ?
C3 C4 C5 F3 179.0(3) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C7 O1 148.1(5) . . . . ?
C3 C4 C7 O2 -34.4(5) . . . . ?
C4 C5 C6 F4 179.0(3) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C5 C4 C7 O1 -32.8(6) . . . . ?
C5 C4 C7 O2 144.8(4) . . . . ?
C6 C1 C2 F1 -180.0(3) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C7 O2 C8 C9 -178.5(4) . . . . ?
C7 C4 C5 F3 -0.3(5) . . . . ?
C7 C4 C5 C6 -178.7(3) . . . . ?
C8 O2 C7 O1 -0.5(7) . . . . ?
C8 O2 C7 C4 -178.0(3) . . . . ?
C8 C9 C10 N4 -64.3(5) . . . . ?
C10 N4 C11 O3 -3.8(5) . . . . ?
C10 N4 C11 C12 174.5(3) . . . . ?
C11 N4 C10 C9 -83.1(4) . . . . ?
C11 C12 C13 C14 174.8(3) . . . . ?
C11 C12 C17 C16 -174.6(3) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C12 C17 C16 1.7(5) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C13 C14 C15 C18 -178.5(4) . . . . ?
C14 C15 C16 C17 -1.6(6) . . . . ?
C15 C16 C17 C12 0.0(6) . . . . ?
C17 C12 C13 C14 -1.7(5) . . . . ?
C18 C15 C16 C17 178.5(4) . . . . ?
