#------------------------------------------------------------------------------
#$Date: 2024-08-29 04:12:01 +0300 (Thu, 29 Aug 2024) $
#$Revision: 294271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/92/7249247.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_7249247
loop_
_publ_author_name
'Janecký, Lukáš'
'Klepetářová, Blanka'
'Beier, Petr'
_publ_section_title
;
 Transformation of 5-acylated N-fluoroalkyl-1,2,3-triazoles to
 trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and
 1,3-oxazin-6-ones via ketenimines.
;
_journal_issue                   37
_journal_name_full               'RSC advances'
_journal_page_first              26938
_journal_page_last               26942
_journal_paper_doi               10.1039/d4ra04794j
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H11 F4 N O2'
_chemical_formula_sum            'C15 H11 F4 N O2'
_chemical_formula_weight         313.25
_chemical_name_systematic
2-fluoro-8-methoxy-2-methyl-5-(trifluoromethyl)-2,3-dihydro-1H-cyclopenta[c]isoquinolin-1-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                109.3028(12)
_cell_angle_beta                 97.3122(13)
_cell_angle_gamma                95.9100(13)
_cell_formula_units_Z            2
_cell_length_a                   4.8502(2)
_cell_length_b                   10.1006(3)
_cell_length_c                   14.4402(5)
_cell_measurement_reflns_used    8520
_cell_measurement_temperature    180
_cell_measurement_theta_max      70.0945
_cell_measurement_theta_min      3.2918
_cell_volume                     654.23(4)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_unetI/netI     0.032
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10818
_diffrn_reflns_theta_full        70.088
_diffrn_reflns_theta_max         70.088
_diffrn_reflns_theta_min         3.292
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.262
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9780
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.0007588
_refine_ls_shift/su_mean         0.0000678
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.24P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0963
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0963
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2292
_reflns_number_total             2461
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.24
_oxford_diffrn_Wilson_scale      5.14
_oxford_refine_ls_scale          0.4462(9)
_cod_data_source_file            d4ra04794j2.cif
_cod_data_source_block           I_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7249247
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0355
_reflns_number_all               2461
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.07357(15) 0.11840(8) 0.75533(6) 0.0318 1.0000 Uani . . . . . .
C2 C 0.3607(2) 0.17174(13) 0.79207(9) 0.0228 1.0000 Uani . . . . . .
C3 C 0.4859(3) 0.06705(14) 0.83253(10) 0.0299 1.0000 Uani . . . . . .
C4 C 0.4980(2) 0.18341(13) 0.70348(9) 0.0219 1.0000 Uani . . . . . .
O5 O 0.4696(2) 0.08894(9) 0.62392(7) 0.0298 1.0000 Uani . . . . . .
C6 C 0.6600(2) 0.32740(12) 0.73659(9) 0.0208 1.0000 Uani . . . . . .
C7 C 0.6000(2) 0.40586(13) 0.82747(9) 0.0214 1.0000 Uani . . . . . .
C8 C 0.3970(3) 0.32340(13) 0.86667(9) 0.0257 1.0000 Uani . . . . . .
N9 N 0.7097(2) 0.54378(11) 0.87821(8) 0.0240 1.0000 Uani . . . . . .
C10 C 0.8866(2) 0.60188(13) 0.83517(9) 0.0226 1.0000 Uani . . . . . .
C11 C 0.9950(3) 0.75823(14) 0.89193(10) 0.0278 1.0000 Uani . . . . . .
F12 F 0.9182(2) 0.83761(8) 0.83752(7) 0.0427 1.0000 Uani . . . . . .
F13 F 1.27654(17) 0.78530(9) 0.91421(6) 0.0370 1.0000 Uani . . . . . .
F14 F 0.89965(19) 0.80728(9) 0.97706(7) 0.0430 1.0000 Uani . . . . . .
C15 C 0.9746(2) 0.53246(12) 0.74315(9) 0.0214 1.0000 Uani . . . . . .
C16 C 0.8545(2) 0.38758(12) 0.69019(9) 0.0204 1.0000 Uani . . . . . .
C17 C 0.9343(2) 0.31012(13) 0.59961(9) 0.0227 1.0000 Uani . . . . . .
C18 C 1.1350(3) 0.37639(13) 0.56304(9) 0.0238 1.0000 Uani . . . . . .
O19 O 1.2355(2) 0.31383(10) 0.47876(7) 0.0298 1.0000 Uani . . . . . .
C20 C 1.1237(3) 0.16773(15) 0.42233(11) 0.0349 1.0000 Uani . . . . . .
C21 C 1.2558(3) 0.52081(14) 0.61454(10) 0.0266 1.0000 Uani . . . . . .
C22 C 1.1776(3) 0.59698(13) 0.70140(10) 0.0253 1.0000 Uani . . . . . .
H31 H 0.6799 0.0992 0.8575 0.0436 1.0000 Uiso R . . . . .
H33 H 0.3987 0.0584 0.8875 0.0424 1.0000 Uiso R . . . . .
H32 H 0.4668 -0.0237 0.7802 0.0422 1.0000 Uiso R . . . . .
H82 H 0.4750 0.3286 0.9338 0.0306 1.0000 Uiso R . . . . .
H81 H 0.2153 0.3589 0.8659 0.0295 1.0000 Uiso R . . . . .
H171 H 0.8542 0.2147 0.5673 0.0298 1.0000 Uiso R . . . . .
H203 H 1.2105 0.1424 0.3658 0.0532 1.0000 Uiso R . . . . .
H201 H 1.1636 0.1129 0.4629 0.0500 1.0000 Uiso R . . . . .
H202 H 0.9187 0.1569 0.3999 0.0514 1.0000 Uiso R . . . . .
H211 H 1.3919 0.5581 0.5864 0.0315 1.0000 Uiso R . . . . .
H221 H 1.2570 0.6931 0.7337 0.0321 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 107.55(10) yes
F1 . C2 . C4 . 107.29(10) yes
C3 . C2 . C4 . 110.65(10) yes
F1 . C2 . C8 . 110.35(9) yes
C3 . C2 . C8 . 114.99(11) yes
C4 . C2 . C8 . 105.78(9) yes
C2 . C3 . H31 . 109.9 no
C2 . C3 . H33 . 111.0 no
H31 . C3 . H33 . 107.0 no
C2 . C3 . H32 . 110.0 no
H31 . C3 . H32 . 107.9 no
H33 . C3 . H32 . 111.0 no
C2 . C4 . O5 . 124.17(11) yes
C2 . C4 . C6 . 106.77(10) yes
O5 . C4 . C6 . 129.07(11) yes
C4 . C6 . C7 . 109.03(10) yes
C4 . C6 . C16 . 130.15(11) yes
C7 . C6 . C16 . 120.81(11) yes
C6 . C7 . C8 . 113.42(10) yes
C6 . C7 . N9 . 124.34(11) yes
C8 . C7 . N9 . 122.25(11) yes
C2 . C8 . C7 . 103.47(10) yes
C2 . C8 . H82 . 111.5 no
C7 . C8 . H82 . 110.8 no
C2 . C8 . H81 . 109.9 no
C7 . C8 . H81 . 110.3 no
H82 . C8 . H81 . 110.7 no
C7 . N9 . C10 . 115.53(10) yes
N9 . C10 . C11 . 114.00(11) yes
N9 . C10 . C15 . 126.18(11) yes
C11 . C10 . C15 . 119.80(11) yes
C10 . C11 . F12 . 110.93(11) yes
C10 . C11 . F13 . 112.25(10) yes
F12 . C11 . F13 . 106.36(11) yes
C10 . C11 . F14 . 112.94(11) yes
F12 . C11 . F14 . 107.13(11) yes
F13 . C11 . F14 . 106.86(11) yes
C10 . C15 . C16 . 117.50(11) yes
C10 . C15 . C22 . 124.55(11) yes
C16 . C15 . C22 . 117.95(11) yes
C15 . C16 . C6 . 115.60(11) yes
C15 . C16 . C17 . 121.17(11) yes
C6 . C16 . C17 . 123.20(11) yes
C16 . C17 . C18 . 118.77(11) yes
C16 . C17 . H171 . 119.1 no
C18 . C17 . H171 . 122.1 no
C17 . C18 . O19 . 124.90(11) yes
C17 . C18 . C21 . 120.80(11) yes
O19 . C18 . C21 . 114.30(11) yes
C18 . O19 . C20 . 117.70(10) yes
O19 . C20 . H203 . 106.6 no
O19 . C20 . H201 . 108.5 no
H203 . C20 . H201 . 112.3 no
O19 . C20 . H202 . 110.4 no
H203 . C20 . H202 . 108.2 no
H201 . C20 . H202 . 110.8 no
C18 . C21 . C22 . 120.86(11) yes
C18 . C21 . H211 . 116.2 no
C22 . C21 . H211 . 122.9 no
C15 . C22 . C21 . 120.44(11) yes
C15 . C22 . H221 . 119.9 no
C21 . C22 . H221 . 119.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.4072(14) yes
C2 . C3 . 1.5093(17) yes
C2 . C4 . 1.5473(17) yes
C2 . C8 . 1.5307(17) yes
C3 . H31 . 0.946 no
C3 . H33 . 0.970 no
C3 . H32 . 0.962 no
C4 . O5 . 1.2072(15) yes
C4 . C6 . 1.4733(16) yes
C6 . C7 . 1.3757(17) yes
C6 . C16 . 1.4214(16) yes
C7 . C8 . 1.5058(16) yes
C7 . N9 . 1.3542(16) yes
C8 . H82 . 0.977 no
C8 . H81 . 0.985 no
N9 . C10 . 1.3190(16) yes
C10 . C11 . 1.5185(17) yes
C10 . C15 . 1.4247(17) yes
C11 . F12 . 1.3424(16) yes
C11 . F13 . 1.3404(15) yes
C11 . F14 . 1.3264(16) yes
C15 . C16 . 1.4272(16) yes
C15 . C22 . 1.4269(17) yes
C16 . C17 . 1.4097(17) yes
C17 . C18 . 1.3803(17) yes
C17 . H171 . 0.937 no
C18 . O19 . 1.3505(15) yes
C18 . C21 . 1.4212(18) yes
O19 . C20 . 1.4365(17) yes
C20 . H203 . 0.939 no
C20 . H201 . 0.947 no
C20 . H202 . 0.989 no
C21 . C22 . 1.3609(19) yes
C21 . H211 . 0.927 no
C22 . H221 . 0.941 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C17 . H171 . O5 . 124 0.94 2.52 3.1427(19) yes
C21 . H211 . O19 2_866 174 0.93 2.57 3.4898(19) yes
