#------------------------------------------------------------------------------
#$Date: 2020-08-05 02:21:14 +0300 (Wed, 05 Aug 2020) $
#$Revision: 254809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038641.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_4038641
loop_
_publ_author_name
'Zhang, Yu'
'Yu, Yue'
'Liang, Bing-Bing'
'Pei, Yong-Yan'
'Liu, Xiang'
'Yao, Hua-Gang'
'Cao, Hua'
_publ_section_title
;
 Synthesis of Pyrrolo[2,1,5-cd]indolizine Rings via Visible-Light-Induced
 Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01253
_journal_year                    2020
_chemical_formula_moiety         'C24 H14 F3 N O'
_chemical_formula_sum            'C24 H14 F3 N O'
_chemical_formula_weight         389.36
_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     direct
_audit_creation_date             2019-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.72(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.308(7)
_cell_length_b                   10.085(2)
_cell_length_c                   8.125(2)
_cell_measurement_reflns_used    877
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      23.1250
_cell_measurement_theta_min      2.7710
_cell_volume                     1737.3(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -68.00  28.00   1.00   10.00    --   11.74 -19.00  90.00   96
  2  ω    -29.00  66.00   1.00   10.00    --   11.74  19.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321409000
_diffrn_orient_matrix_UB_12      -0.0143816000
_diffrn_orient_matrix_UB_13      0.0073642000
_diffrn_orient_matrix_UB_21      -0.0092674000
_diffrn_orient_matrix_UB_22      0.0480773000
_diffrn_orient_matrix_UB_23      -0.0614736000
_diffrn_orient_matrix_UB_31      0.0006057000
_diffrn_orient_matrix_UB_32      -0.0493513000
_diffrn_orient_matrix_UB_33      -0.0620800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7224
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.236
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0883
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1596P)²+16.0455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.2242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1949
_reflns_number_total             3062
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01253_si_001.cif
_cod_data_source_block           exp_1892
_cod_original_cell_volume        1737.4(8)
_cod_database_code               4038641
_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.
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C3: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C17(H17), C13(H13), C16(H16), C00D(H00D), C21(H21), C22(H22),
 C11(H11), C14(H14), C19(H19), C4(H4), C23(H23), C3(H3), C2(H2)
;
_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 1.681
_oxdiff_exptl_absorpt_empirical_full_min 0.491
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
F3 F 0.49760(17) 1.0123(4) 0.2842(5) 0.0569(12) Uani 1 1 d . . . . .
F2 F 0.48071(16) 0.8098(4) 0.3370(6) 0.0607(12) Uani 1 1 d . . . . .
N1 N 0.86300(18) 0.7404(5) 0.7025(5) 0.0290(11) Uani 1 1 d . . . . .
F1 F 0.51431(18) 0.8653(6) 0.1082(5) 0.0864(17) Uani 1 1 d . . . . .
O1 O 0.9219(2) 0.3530(5) 0.8781(6) 0.0564(14) Uani 1 1 d . . . . .
C10 C 0.7769(2) 0.8268(5) 0.5666(6) 0.0267(13) Uani 1 1 d . . . . .
C24 C 0.6501(3) 0.4020(5) 0.4961(6) 0.0301(14) Uani 1 1 d . . . . .
H24 H 0.608320 0.412717 0.517154 0.036 Uiso 1 1 calc R . . . .
C17 C 0.6835(2) 0.7496(5) 0.3742(5) 0.0226(12) Uani 1 1 d . . . . .
H17 H 0.706532 0.675988 0.346770 0.027 Uiso 1 1 calc R . . . .
C12 C 0.7120(2) 0.8424(5) 0.4816(6) 0.0279(13) Uani 1 1 d . . . . .
C20 C 0.7588(2) 0.4701(5) 0.5469(6) 0.0289(13) Uani 1 1 d . . . . .
C13 C 0.6782(2) 0.9588(5) 0.5182(6) 0.0280(13) Uani 1 1 d . . . . .
H13 H 0.697414 1.024040 0.586768 0.034 Uiso 1 1 calc R . . . .
C16 C 0.6213(2) 0.7626(5) 0.3054(6) 0.0262(13) Uani 1 1 d . . . . .
H16 H 0.602852 0.697871 0.234652 0.031 Uiso 1 1 calc R . . . .
C00D C 0.6957(2) 0.4844(5) 0.5719(6) 0.0273(13) Uani 1 1 d . . . . .
H00D H 0.683861 0.551261 0.641422 0.033 Uiso 1 1 calc R . . . .
C21 C 0.7759(2) 0.3687(5) 0.4433(6) 0.0301(13) Uani 1 1 d . . . . .
H21 H 0.817927 0.356236 0.425666 0.036 Uiso 1 1 calc R . . . .
C1 C 0.8714(2) 0.8740(5) 0.7114(6) 0.0294(13) Uani 1 1 d . . . . .
C6 C 0.8644(2) 0.5214(5) 0.7193(6) 0.0291(13) Uani 1 1 d . . . . .
C22 C 0.7287(3) 0.2852(5) 0.3654(6) 0.0295(14) Uani 1 1 d . . . . .
H22 H 0.739666 0.216765 0.297086 0.035 Uiso 1 1 calc R . . . .
C7 C 0.8084(2) 0.5611(5) 0.6231(6) 0.0280(13) Uani 1 1 d . . . . .
C11 C 0.8167(2) 0.9281(5) 0.6247(6) 0.0300(13) Uani 1 1 d . . . . .
H11 H 0.808737 1.018150 0.608974 0.036 Uiso 1 1 calc R . . . .
C15 C 0.5867(3) 0.8753(5) 0.3446(6) 0.0286(13) Uani 1 1 d . . . . .
C8 C 0.8070(2) 0.7011(6) 0.6169(6) 0.0308(13) Uani 1 1 d . . . . .
C14 C 0.6162(3) 0.9734(5) 0.4502(7) 0.0347(14) Uani 1 1 d . . . . .
H14 H 0.593763 1.048830 0.474312 0.042 Uiso 1 1 calc R . . . .
C18 C 0.5221(3) 0.8924(6) 0.2694(6) 0.0376(15) Uani 1 1 d . . . . .
C19 C 0.8785(3) 0.3849(6) 0.7756(7) 0.0403(16) Uani 1 1 d . . . . .
H19 H 0.852436 0.317759 0.729837 0.048 Uiso 1 1 calc R . . . .
C4 C 0.9551(3) 0.6793(7) 0.8646(7) 0.0390(16) Uani 1 1 d . . . . .
H4 H 0.982736 0.617792 0.917553 0.047 Uiso 1 1 calc R . . . .
C23 C 0.6654(3) 0.3052(6) 0.3908(7) 0.0346(15) Uani 1 1 d . . . . .
H23 H 0.634034 0.252651 0.336070 0.041 Uiso 1 1 calc R . . . .
C5 C 0.8983(3) 0.6366(6) 0.7686(7) 0.0367(15) Uani 1 1 d . . . . .
C3 C 0.9677(3) 0.8124(6) 0.8764(7) 0.0429(7) Uani 1 1 d . U . . .
H3 H 1.005053 0.838523 0.936699 0.051 Uiso 1 1 calc R . . . .
C2 C 0.9285(3) 0.9110(7) 0.8046(7) 0.0426(7) Uani 1 1 d . U . . .
H2 H 0.939541 0.999898 0.817349 0.051 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 0.0033 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
C1 N1 C8 114.5(4) . . ?
C1 N1 C5 132.3(4) . . ?
C5 N1 C8 113.2(5) . . ?
C11 C10 C12 126.2(5) . . ?
C11 C10 C8 108.0(4) . . ?
C8 C10 C12 125.6(4) . . ?
C00D C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C00D 120.9(5) . . ?
C12 C17 H17 118.9 . . ?
C12 C17 C16 122.2(5) . . ?
C16 C17 H17 118.9 . . ?
C17 C12 C10 123.5(4) . . ?
C17 C12 C13 119.5(5) . . ?
C13 C12 C10 117.0(4) . . ?
C00D C20 C21 118.6(5) . . ?
C00D C20 C7 122.2(5) . . ?
C21 C20 C7 119.2(5) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
C17 C16 H16 120.5 . . ?
C17 C16 C15 118.9(4) . . ?
C15 C16 H16 120.5 . . ?
C24 C00D C20 121.5(5) . . ?
C24 C00D H00D 119.3 . . ?
C20 C00D H00D 119.3 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(5) . . ?
C22 C21 H21 120.3 . . ?
N1 C1 C11 105.1(4) . . ?
N1 C1 C2 113.0(5) . . ?
C11 C1 C2 141.9(5) . . ?
C7 C6 C19 124.7(5) . . ?
C5 C6 C7 107.7(5) . . ?
C5 C6 C19 127.0(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 119.9 . . ?
C6 C7 C20 125.4(5) . . ?
C8 C7 C20 126.2(4) . . ?
C8 C7 C6 108.3(4) . . ?
C10 C11 C1 109.5(5) . . ?
C10 C11 H11 125.3 . . ?
C1 C11 H11 125.3 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 C18 119.6(5) . . ?
C14 C15 C18 121.0(5) . . ?
N1 C8 C10 103.1(4) . . ?
N1 C8 C7 104.8(4) . . ?
C7 C8 C10 152.1(5) . . ?
C13 C14 C15 121.0(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
F3 C18 F2 104.1(4) . . ?
F3 C18 F1 105.3(5) . . ?
F3 C18 C15 115.7(5) . . ?
F2 C18 C15 112.3(5) . . ?
F1 C18 F2 104.3(5) . . ?
F1 C18 C15 114.0(5) . . ?
O1 C19 C6 125.1(6) . . ?
O1 C19 H19 117.5 . . ?
C6 C19 H19 117.5 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(5) . . ?
C24 C23 C22 119.4(5) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
N1 C5 C6 105.9(4) . . ?
N1 C5 C4 112.6(5) . . ?
C6 C5 C4 141.5(5) . . ?
C4 C3 H3 117.7 . . ?
C4 C3 C2 124.5(5) . . ?
C2 C3 H3 117.7 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.5 . . ?
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
F3 C18 1.327(7) . ?
F2 C18 1.368(7) . ?
N1 C1 1.360(7) . ?
N1 C8 1.378(6) . ?
N1 C5 1.367(7) . ?
F1 C18 1.332(6) . ?
O1 C19 1.223(7) . ?
C10 C12 1.492(7) . ?
C10 C11 1.381(7) . ?
C10 C8 1.461(7) . ?
C24 H24 0.9300 . ?
C24 C00D 1.376(7) . ?
C24 C23 1.359(8) . ?
C17 H17 0.9300 . ?
C17 C12 1.378(7) . ?
C17 C16 1.392(7) . ?
C12 C13 1.424(7) . ?
C20 C00D 1.389(7) . ?
C20 C21 1.395(7) . ?
C20 C7 1.486(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.408(7) . ?
C00D H00D 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.413(7) . ?
C1 C11 1.410(7) . ?
C1 C2 1.417(7) . ?
C6 C7 1.418(7) . ?
C6 C19 1.472(8) . ?
C6 C5 1.405(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.399(8) . ?
C7 C8 1.414(8) . ?
C11 H11 0.9300 . ?
C15 C14 1.416(7) . ?
C15 C18 1.458(8) . ?
C14 H14 0.9300 . ?
C19 H19 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.439(8) . ?
C4 C3 1.371(9) . ?
C23 H23 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.390(9) . ?
C2 H2 0.9300 . ?
