#------------------------------------------------------------------------------
#$Date: 2025-02-01 09:07:15 +0200 (Sat, 01 Feb 2025) $
#$Revision: 297561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129628.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_7129628
loop_
_publ_author_name
'Mo, Kangdong'
'Zhou, Xiaocong'
'Wu, Ju'
'Zhao, Yufen'
_publ_section_title
;
 Radical-induced denitration of
 N-(p-nitrophenyl)propiolamides coupled with
 dearomatization: access to phosphonylated/trifluoromethylated
 azaspiro[4.5]-trienones.
;
_journal_issue                   9
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1306
_journal_page_last               1309
_journal_paper_doi               10.1039/d1cc05724c
_journal_volume                  58
_journal_year                    2021
_chemical_formula_moiety         'C17 H12 F3 N O2'
_chemical_formula_sum            'C17 H12 F3 N O2'
_chemical_formula_weight         319.28
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2827qb
_audit_creation_date             2021-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.003(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1738(8)
_cell_length_b                   6.7235(4)
_cell_length_c                   15.9099(8)
_cell_measurement_reflns_used    9109
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      68.49
_cell_measurement_theta_min      3.18
_cell_volume                     1488.30(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      208.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25179
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.514
_diffrn_reflns_theta_min         3.176
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.649
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5386
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1401 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.7152.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             782
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0460
_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)+(0.0758P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2126
_reflns_number_total             2779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc05724c2.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H F N O P'
_cod_original_formula_weight         93.00
_cod_original_formula_moiety         '0.24(C17 H12 F3 N O2)'
_cod_original_formula_units_Z            17
_cod_database_code               7129628
_shelx_shelxl_version_number     2018/3
_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 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00G)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
F001 F 0.46521(9) 0.4412(2) 0.90755(8) 0.0666(4) Uani 1 1 d . . . . .
O002 O 0.47259(9) 0.6192(2) 0.71774(9) 0.0505(4) Uani 1 1 d . . . . .
F003 F 0.31835(10) 0.4762(3) 0.91877(8) 0.0830(6) Uani 1 1 d . . . . .
F004 F 0.39398(12) 0.7155(3) 0.87320(10) 0.0808(5) Uani 1 1 d . . . . .
O005 O 0.11195(10) -0.1812(2) 0.53814(10) 0.0578(4) Uani 1 1 d . . . . .
N006 N 0.35976(9) 0.4117(2) 0.63996(9) 0.0368(4) Uani 1 1 d . . . . .
C007 C 0.28156(11) 0.3185(3) 0.74980(10) 0.0339(4) Uani 1 1 d . . . . .
C008 C 0.28588(10) 0.2724(3) 0.65561(10) 0.0323(4) Uani 1 1 d . . . . .
C009 C 0.40508(11) 0.5055(3) 0.71206(11) 0.0375(4) Uani 1 1 d . . . . .
C00A C 0.16523(12) -0.0437(3) 0.56795(11) 0.0394(4) Uani 1 1 d . . . . .
C00B C 0.35163(11) 0.4452(3) 0.78027(10) 0.0366(4) Uani 1 1 d . . . . .
C00C C 0.18984(11) 0.3111(3) 0.59854(10) 0.0362(4) Uani 1 1 d . . . . .
H00C H 0.168445 0.443044 0.589422 0.043 Uiso 1 1 calc R . . . .
C00D C 0.32000(11) 0.0616(3) 0.65193(10) 0.0362(4) Uani 1 1 d . . . . .
H00D H 0.383228 0.030294 0.678739 0.043 Uiso 1 1 calc R . . . .
C00E C 0.26433(12) -0.0824(3) 0.61226(11) 0.0399(4) Uani 1 1 d . . . . .
H00E H 0.288990 -0.212285 0.612580 0.048 Uiso 1 1 calc R . . . .
C00F C 0.13432(11) 0.1646(3) 0.56064(11) 0.0396(4) Uani 1 1 d . . . . .
H00F H 0.073473 0.195664 0.528221 0.047 Uiso 1 1 calc R . . . .
C00G C 0.20731(12) 0.2253(3) 0.79115(10) 0.0402(4) Uani 1 1 d . . . . .
C00H C 0.39167(13) 0.4240(3) 0.55855(12) 0.0483(5) Uani 1 1 d . . . . .
H00A H 0.416766 0.296011 0.545254 0.072 Uiso 1 1 calc GR . . . .
H00B H 0.441686 0.523897 0.562257 0.072 Uiso 1 1 calc GR . . . .
H00G H 0.337857 0.460393 0.513816 0.072 Uiso 1 1 calc GR . . . .
C00I C 0.38157(13) 0.5185(4) 0.86976(12) 0.0476(5) Uani 1 1 d . . . . .
C00J C 0.12353(15) 0.3268(5) 0.79441(15) 0.0665(7) Uani 1 1 d . . . . .
H00J H 0.113488 0.454745 0.770548 0.080 Uiso 1 1 calc R . . . .
C00K C 0.22013(19) 0.0367(4) 0.82524(15) 0.0628(6) Uani 1 1 d . . . . .
H00K H 0.276252 -0.034968 0.821992 0.075 Uiso 1 1 calc R . . . .
C00L C 0.0680(2) 0.0531(7) 0.86768(17) 0.0956(13) Uani 1 1 d . . . . .
H00L H 0.020612 -0.005201 0.893775 0.115 Uiso 1 1 calc R . . . .
C00M C 0.1499(3) -0.0478(5) 0.86455(19) 0.0890(10) Uani 1 1 d . . . . .
H00M H 0.159388 -0.175228 0.888958 0.107 Uiso 1 1 calc R . . . .
C00N C 0.05385(17) 0.2387(7) 0.83325(18) 0.0912(12) Uani 1 1 d . . . . .
H00N H -0.003235 0.307769 0.835709 0.109 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C009 N006 C008 113.11(13) . . ?
C009 N006 C00H 123.28(15) . . ?
C00H N006 C008 122.90(15) . . ?
C00B C007 C008 108.54(14) . . ?
C00B C007 C00G 130.85(16) . . ?
C00G C007 C008 120.61(15) . . ?
N006 C008 C007 101.49(13) . . ?
N006 C008 C00C 112.40(14) . . ?
N006 C008 C00D 110.59(13) . . ?
C00C C008 C007 110.59(12) . . ?
C00D C008 C007 107.46(14) . . ?
C00D C008 C00C 113.54(15) . . ?
O002 C009 N006 126.44(16) . . ?
O002 C009 C00B 128.21(17) . . ?
N006 C009 C00B 105.31(14) . . ?
O005 C00A C00E 120.78(19) . . ?
O005 C00A C00F 122.38(17) . . ?
C00F C00A C00E 116.84(16) . . ?
C007 C00B C009 110.89(15) . . ?
C007 C00B C00I 128.16(17) . . ?
C00I C00B C009 120.89(16) . . ?
C00F C00C C008 122.22(18) . . ?
C00E C00D C008 122.64(15) . . ?
C00D C00E C00A 121.64(18) . . ?
C00C C00F C00A 121.95(16) . . ?
C00J C00G C007 119.8(2) . . ?
C00K C00G C007 120.82(18) . . ?
C00K C00G C00J 119.4(2) . . ?
F001 C00I F004 105.66(17) . . ?
F001 C00I C00B 111.72(17) . . ?
F003 C00I F001 107.15(18) . . ?
F003 C00I F004 106.68(18) . . ?
F003 C00I C00B 112.95(16) . . ?
F004 C00I C00B 112.22(18) . . ?
C00G C00J C00N 119.7(3) . . ?
C00G C00K C00M 120.0(3) . . ?
C00M C00L C00N 120.4(2) . . ?
C00L C00M C00K 120.2(3) . . ?
C00L C00N C00J 120.4(3) . . ?
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
F001 C00I 1.328(2) . ?
O002 C009 1.215(2) . ?
F003 C00I 1.326(2) . ?
F004 C00I 1.336(3) . ?
O005 C00A 1.230(2) . ?
N006 C008 1.461(2) . ?
N006 C009 1.358(2) . ?
N006 C00H 1.454(2) . ?
C007 C008 1.543(2) . ?
C007 C00B 1.328(3) . ?
C007 C00G 1.482(2) . ?
C008 C00C 1.508(2) . ?
C008 C00D 1.502(3) . ?
C009 C00B 1.493(2) . ?
C00A C00E 1.470(2) . ?
C00A C00F 1.465(3) . ?
C00B C00I 1.490(3) . ?
C00C C00F 1.331(3) . ?
C00D C00E 1.330(3) . ?
C00G C00J 1.379(3) . ?
C00G C00K 1.377(3) . ?
C00J C00N 1.393(4) . ?
C00K C00M 1.394(4) . ?
C00L C00M 1.353(5) . ?
C00L C00N 1.362(5) . ?
