#------------------------------------------------------------------------------
#$Date: 2020-09-04 02:29:06 +0300 (Fri, 04 Sep 2020) $
#$Revision: 255853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038728.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_4038728
loop_
_publ_author_name
'Liu, Liang'
'Yang, De-Yong'
'He, Yan-Hong'
'Guan, Zhi'
_publ_section_title
;
 Redox-Neutral Photocatalytic Radical Cascade Cyclization for the
 Synthesis of
 CH₂CN/CF₂COOEt/CF₃-Containing
 Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-One Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01688
_journal_year                    2020
_chemical_formula_moiety         'C21 H18 F2 N2 O3'
_chemical_formula_sum            'C21 H20 F0.25 N O6'
_chemical_formula_weight         387.13
_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     iterative
_audit_creation_date             2019-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.7154(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8490(2)
_cell_length_b                   11.07235(14)
_cell_length_c                   13.3470(2)
_cell_measurement_reflns_used    5846
_cell_measurement_temperature    292(1)
_cell_measurement_theta_max      71.6400
_cell_measurement_theta_min      3.9940
_cell_volume                     1844.71(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.00    --  -35.97  57.00-180.00   84
  2  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
  3  ω     24.00  90.00   1.00    1.00    --   35.97-126.00-150.00   66
  4  ω    -31.00  53.00   1.00    1.00    --   35.97 -57.00-120.00   84
  5  ω     24.00  90.00   1.00    1.00    --   35.97-126.00  90.00   66
  6  ω     24.00  90.00   1.00    1.00    --   35.97-126.00 -30.00   66
  7  ω     40.00 135.00   1.00    1.75    --  107.97 -77.00 -30.00   95
  8  ω     41.00 126.00   1.00    1.75    --  107.97 -61.00  90.00   85
  9  ω     81.00 176.00   1.00    1.75    --  107.97  77.00  90.00   95
 10  ω     87.00 178.00   1.00    1.75    --  107.97  30.00   0.00   91
 11  ω     38.00 112.00   1.00    1.75    --  107.97-112.00 -60.00   74
 12  ω     40.00 125.00   1.00    1.75    --  107.97 -45.00 -60.00   85
 13  ω     39.00 110.00   1.00    1.75    --  107.97 -95.00  60.00   71
 14  ω     57.00 150.00   1.00    1.75    --  107.97 178.00 -30.00   93
 15  ω   -104.00 -20.00   1.00    1.00    --  -35.97 -77.00 -30.00   84
 16  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0492946000
_diffrn_orient_matrix_UB_12      -0.1157461000
_diffrn_orient_matrix_UB_13      0.0332588000
_diffrn_orient_matrix_UB_21      0.1017419000
_diffrn_orient_matrix_UB_22      -0.0197251000
_diffrn_orient_matrix_UB_23      0.0865145000
_diffrn_orient_matrix_UB_31      -0.0495474000
_diffrn_orient_matrix_UB_32      0.0746643000
_diffrn_orient_matrix_UB_33      0.0743061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10572
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.741
_diffrn_reflns_theta_min         3.541
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             813
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0393
_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)+(0.0585P)²+0.1806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3099
_reflns_number_total             3563
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01688_si_002.cif
_cod_data_source_block           gz190525
_cod_original_cell_volume        1844.72(5)
_cod_database_code               4038728
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_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.
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3AA-F1
 1.45 with sigma of 0.02
 C3AA-F6A
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F1A: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008
F6A \\sim F6: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008
4. Others
 Sof(F6A)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(F6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C4AA(H4AA)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2019-05-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.833
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 0.1278(15) 0.1323(12) 0.2456(11) 0.094(2) Uani 0.45(4) 1 d D U P A 1
O2 O 0.10927(8) 0.28159(9) 0.39196(8) 0.0678(3) Uani 1 1 d . . . . .
N N 0.37181(9) 0.00647(9) 0.32633(8) 0.0525(3) Uani 1 1 d . . . . .
O4 O 0.24577(9) -0.11649(10) 0.23216(8) 0.0779(3) Uani 1 1 d . . . . .
O5 O -0.01701(10) 0.16581(11) 0.43230(11) 0.0899(4) Uani 1 1 d . . . . .
F6 F -0.0336(15) 0.080(2) 0.2447(15) 0.114(3) Uani 0.45(4) 1 d . U P A 1
N7 N 0.49638(9) 0.14325(9) 0.39939(9) 0.0572(3) Uani 1 1 d . . . . .
C1 C 0.25814(10) 0.03562(10) 0.48203(9) 0.0491(3) Uani 1 1 d . . . . .
C0AA C 0.35013(10) 0.10397(10) 0.48602(9) 0.0486(3) Uani 1 1 d . . . . .
C3 C 0.40897(10) 0.08870(10) 0.40670(10) 0.0498(3) Uani 1 1 d . . . . .
C1AA C 0.04861(11) 0.18520(13) 0.38427(12) 0.0634(3) Uani 1 1 d . . . . .
C2 C 0.44482(11) 0.01150(12) 0.26313(10) 0.0568(3) Uani 1 1 d . . . . .
C2AA C 0.21562(10) -0.05468(11) 0.39538(10) 0.0540(3) Uani 1 1 d . . . . .
C5AA C 0.27664(11) -0.05744(12) 0.30979(11) 0.0570(3) Uani 1 1 d . . . . .
C4 C 0.38655(11) 0.18483(11) 0.56710(10) 0.0573(3) Uani 1 1 d . . . . .
H4 H 0.447795 0.230492 0.569288 0.069 Uiso 1 1 calc R . . . .
C5 C 0.20550(11) 0.04850(12) 0.56128(11) 0.0585(3) Uani 1 1 d . . . . .
H5 H 0.144905 0.002253 0.560534 0.070 Uiso 1 1 calc R . . . .
C6 C 0.52061(11) 0.09628(12) 0.31014(11) 0.0582(3) Uani 1 1 d . . . . .
C3AA C 0.06880(13) 0.09401(15) 0.30466(13) 0.0709(4) Uani 1 1 d D . . . .
C8 C 0.33220(13) 0.19710(13) 0.64360(11) 0.0650(4) Uani 1 1 d . . . . .
H8 H 0.356349 0.251462 0.697185 0.078 Uiso 1 1 calc R . . . .
C9 C 0.45120(14) -0.05080(14) 0.17446(11) 0.0688(4) Uani 1 1 d . . . . .
H9 H 0.400475 -0.108079 0.144278 0.083 Uiso 1 1 calc R . . . .
C14 C 0.09653(11) -0.03231(13) 0.34387(12) 0.0645(4) Uani 1 1 d . . . . .
H14A H 0.075167 -0.087873 0.286485 0.077 Uiso 1 1 calc R . . . .
H14B H 0.054504 -0.051442 0.393319 0.077 Uiso 1 1 calc R . . . .
C10 C 0.24177(12) 0.12877(12) 0.64094(11) 0.0634(4) Uani 1 1 d . . . . .
H10 H 0.205215 0.136858 0.692935 0.076 Uiso 1 1 calc R . . . .
C11 C 0.60575(13) 0.12505(14) 0.26640(14) 0.0746(4) Uani 1 1 d . . . . .
H11 H 0.656273 0.182936 0.295734 0.089 Uiso 1 1 calc R . . . .
C12 C 0.22736(13) -0.18440(12) 0.44010(13) 0.0670(4) Uani 1 1 d . . . . .
H12A H 0.301755 -0.201743 0.468277 0.101 Uiso 1 1 calc GR . . . .
H12B H 0.198591 -0.241136 0.386259 0.101 Uiso 1 1 calc GR . . . .
H12C H 0.189006 -0.190732 0.493464 0.101 Uiso 1 1 calc GR . . . .
C13 C 0.53741(16) -0.02247(17) 0.13396(13) 0.0814(5) Uani 1 1 d . . . . .
H13 H 0.545776 -0.062806 0.075253 0.098 Uiso 1 1 calc R . . . .
C4AA C 0.61206(16) 0.06446(17) 0.17820(15) 0.0845(5) Uani 1 1 d . . . . .
H4AA H 0.667929 0.082197 0.147263 0.101 Uiso 1 1 calc R . . . .
C15 C 0.09489(16) 0.37065(14) 0.46796(14) 0.0795(5) Uani 1 1 d . . . . .
H15A H 0.097029 0.331498 0.533432 0.095 Uiso 1 1 calc R . . . .
H15B H 0.026047 0.410344 0.445013 0.095 Uiso 1 1 calc R . . . .
C16 C 0.18232(17) 0.46014(16) 0.47999(17) 0.0950(6) Uani 1 1 d . . . . .
H16A H 0.178478 0.499793 0.415255 0.142 Uiso 1 1 calc GR . . . .
H16B H 0.250100 0.419878 0.501700 0.142 Uiso 1 1 calc GR . . . .
H16C H 0.175163 0.518881 0.530840 0.142 Uiso 1 1 calc GR . . . .
F6A F -0.0198(12) 0.0978(15) 0.2203(11) 0.104(2) Uani 0.55(4) 1 d D U P A 2
F1A F 0.1528(8) 0.1404(8) 0.2632(7) 0.0688(14) Uani 0.55(4) 1 d . U P A 2
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'
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
C1AA O2 C15 115.73(12) . . ?
C3 N C2 106.21(11) . . ?
C5AA N C3 125.57(11) . . ?
C5AA N C2 127.98(11) . . ?
C3 N7 C6 105.17(11) . . ?
C0AA C1 C2AA 122.13(11) . . ?
C5 C1 C0AA 118.43(11) . . ?
C5 C1 C2AA 119.43(11) . . ?
C1 C0AA C3 119.56(11) . . ?
C1 C0AA C4 120.19(12) . . ?
C4 C0AA C3 120.24(11) . . ?
N C3 C0AA 119.52(11) . . ?
N7 C3 N 112.84(11) . . ?
N7 C3 C0AA 127.63(12) . . ?
O2 C1AA C3AA 113.30(13) . . ?
O5 C1AA O2 125.94(15) . . ?
O5 C1AA C3AA 120.76(14) . . ?
C6 C2 N 104.60(11) . . ?
C9 C2 N 132.48(14) . . ?
C9 C2 C6 122.90(13) . . ?
C1 C2AA C5AA 115.03(10) . . ?
C1 C2AA C14 111.79(10) . . ?
C1 C2AA C12 109.29(11) . . ?
C5AA C2AA C14 107.46(11) . . ?
C5AA C2AA C12 104.39(10) . . ?
C14 C2AA C12 108.45(11) . . ?
N C5AA C2AA 117.38(11) . . ?
O4 C5AA N 120.71(13) . . ?
O4 C5AA C2AA 121.86(12) . . ?
C8 C4 C0AA 120.22(13) . . ?
C10 C5 C1 121.05(13) . . ?
C2 C6 N7 111.18(11) . . ?
C2 C6 C11 120.05(14) . . ?
C11 C6 N7 128.77(14) . . ?
F1 C3AA F6 107.6(8) . . ?
F1 C3AA C1AA 115.4(7) . . ?
F1 C3AA C14 113.2(6) . . ?
F6 C3AA C1AA 100.6(9) . . ?
F6 C3AA C14 102.1(9) . . ?
C14 C3AA C1AA 115.85(14) . . ?
F6A C3AA C1AA 107.4(7) . . ?
F6A C3AA C14 112.8(7) . . ?
F6A C3AA F1A 103.0(6) . . ?
F1A C3AA C1AA 107.5(4) . . ?
F1A C3AA C14 109.4(4) . . ?
C4 C8 C10 120.00(13) . . ?
C13 C9 C2 115.87(17) . . ?
C3AA C14 C2AA 115.60(12) . . ?
C5 C10 C8 120.11(13) . . ?
C4AA C11 C6 117.32(17) . . ?
C9 C13 C4AA 121.96(16) . . ?
C11 C4AA C13 121.86(15) . . ?
O2 C15 C16 108.10(14) . . ?
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 C3AA 1.288(11) . ?
O2 C1AA 1.3111(17) . ?
O2 C15 1.4576(18) . ?
N C3 1.4017(16) . ?
N C2 1.4035(16) . ?
N C5AA 1.3845(17) . ?
O4 C5AA 1.2097(16) . ?
O5 C1AA 1.1935(18) . ?
F6 C3AA 1.377(16) . ?
N7 C3 1.2992(16) . ?
N7 C6 1.4008(18) . ?
C1 C0AA 1.3938(17) . ?
C1 C2AA 1.5284(17) . ?
C1 C5 1.3914(18) . ?
C0AA C3 1.4493(17) . ?
C0AA C4 1.3969(18) . ?
C1AA C3AA 1.532(2) . ?
C2 C6 1.391(2) . ?
C2 C9 1.389(2) . ?
C2AA C5AA 1.5315(18) . ?
C2AA C14 1.5417(19) . ?
C2AA C12 1.5490(18) . ?
C4 C8 1.374(2) . ?
C5 C10 1.3793(19) . ?
C6 C11 1.3936(19) . ?
C3AA C14 1.506(2) . ?
C3AA F6A 1.399(12) . ?
C3AA F1A 1.420(8) . ?
C8 C10 1.380(2) . ?
C9 C13 1.379(2) . ?
C11 C4AA 1.374(3) . ?
C13 C4AA 1.388(3) . ?
C15 C16 1.478(2) . ?
