#------------------------------------------------------------------------------
#$Date: 2020-05-27 02:13:35 +0300 (Wed, 27 May 2020) $
#$Revision: 252361 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038408.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_4038408
loop_
_publ_author_name
'Nagireddy, Attunuri'
'Singam, Maneesh Kumar Reddy'
'Nanubolu, Jagadeesh Babu'
'Sridhar Reddy, Maddi'
_publ_section_title
;
 Base Mediated Cyclopentannulation of Ynones with Amino Crotonates for
 Regio- & Stereoselective Synthesis of Pentafulvenes and
 Cyclopenta[c]quinolines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00203
_journal_year                    2020
_chemical_formula_moiety         'C26 H20 F N O2'
_chemical_formula_sum            'C26 H20 F N O2'
_chemical_formula_weight         397.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 103.67(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.920(8)
_cell_length_b                   13.754(12)
_cell_length_c                   17.019(17)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.959
_cell_measurement_theta_min      2.4595
_cell_volume                     2029(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22775
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.381
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0580
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3378
_reflns_number_total             4661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00203_si_001.cif
_cod_data_source_block           KA831_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038408
_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.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.4560(2) 0.90368(14) 0.60704(14) 0.0470(5) Uani 1 1 d . . . . .
C2 C 0.4437(3) 0.88160(17) 0.68312(14) 0.0519(6) Uani 1 1 d . . . . .
H2 H 0.404946 0.926351 0.714210 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4905(3) 0.79093(17) 0.71226(13) 0.0492(5) Uani 1 1 d . . . . .
H3 H 0.482787 0.773700 0.763993 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5490(2) 0.72468(14) 0.66637(11) 0.0394(5) Uani 1 1 d . . . . .
H4 H 0.580256 0.663652 0.687550 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5614(2) 0.74835(12) 0.58877(10) 0.0308(4) Uani 1 1 d . . . . .
C6 C 0.5126(2) 0.84021(14) 0.55890(12) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.518275 0.858295 0.507023 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6113(2) 0.67453(12) 0.53685(10) 0.0291(4) Uani 1 1 d . . . . .
C8 C 0.73060(19) 0.60608(12) 0.55654(10) 0.0282(4) Uani 1 1 d . . . . .
C9 C 0.71331(19) 0.54073(12) 0.48729(10) 0.0275(4) Uani 1 1 d . . . . .
C10 C 0.58770(19) 0.57861(13) 0.42481(10) 0.0287(4) Uani 1 1 d . . . . .
C11 C 0.5279(2) 0.65746(13) 0.45662(10) 0.0313(4) Uani 1 1 d . . . . .
H11 H 0.444443 0.694306 0.429198 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5355(2) 0.54213(12) 0.34142(10) 0.0306(4) Uani 1 1 d . . . . .
C13 C 0.3795(2) 0.54531(14) 0.30204(12) 0.0394(5) Uani 1 1 d . . . . .
H13 H 0.308282 0.570092 0.328869 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3297(3) 0.51203(17) 0.22362(13) 0.0530(6) Uani 1 1 d . . . . .
H14 H 0.225337 0.514978 0.198236 0.064 Uiso 1 1 calc R U . . .
C15 C 0.4320(3) 0.47462(17) 0.18250(12) 0.0530(6) Uani 1 1 d . . . . .
H15 H 0.397012 0.450786 0.130235 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5872(3) 0.47284(15) 0.21961(12) 0.0443(5) Uani 1 1 d . . . . .
H16 H 0.657400 0.448602 0.191944 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6389(2) 0.50701(13) 0.29800(11) 0.0354(4) Uani 1 1 d . . . . .
H17 H 0.743986 0.506550 0.322029 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8609(2) 0.60726(13) 0.62592(10) 0.0327(4) Uani 1 1 d . . . . .
C19 C 0.9966(3) 0.6964(2) 0.73977(17) 0.0741(8) Uani 1 1 d . . . . .
H19A H 1.091999 0.696753 0.722926 0.111 Uiso 1 1 calc R U . . .
H19B H 0.995299 0.642068 0.775026 0.111 Uiso 1 1 calc R U . . .
H19C H 0.987195 0.755689 0.767970 0.111 Uiso 1 1 calc R U . . .
C20 C 0.7768(2) 0.45068(12) 0.47932(10) 0.0295(4) Uani 1 1 d . . . . .
H20 H 0.737769 0.418237 0.430851 0.035 Uiso 1 1 calc R U . . .
C21 C 0.9490(2) 0.31228(12) 0.52252(10) 0.0295(4) Uani 1 1 d . . . . .
C22 C 1.0863(2) 0.28561(13) 0.57528(10) 0.0331(4) Uani 1 1 d . . . . .
H22 H 1.132396 0.327086 0.617198 0.040 Uiso 1 1 calc R U . . .
C23 C 1.1547(2) 0.19788(14) 0.56590(12) 0.0405(5) Uani 1 1 d . . . . .
H23 H 1.247259 0.180818 0.601314 0.049 Uiso 1 1 calc R U . . .
C24 C 1.0876(3) 0.13560(15) 0.50489(14) 0.0493(5) Uani 1 1 d . . . . .
H24 H 1.134627 0.076780 0.498371 0.059 Uiso 1 1 calc R U . . .
C25 C 0.9500(3) 0.16100(16) 0.45347(15) 0.0564(6) Uani 1 1 d . . . . .
H25 H 0.903158 0.118261 0.412691 0.068 Uiso 1 1 calc R U . . .
C26 C 0.8800(2) 0.24888(15) 0.46123(13) 0.0465(5) Uani 1 1 d . . . . .
H26 H 0.787406 0.265416 0.425645 0.056 Uiso 1 1 calc R U . . .
H1N H 0.938(3) 0.4394(16) 0.5784(14) 0.046(6) Uiso 1 1 d . . . . .
N1 N 0.88714(18) 0.40488(11) 0.53287(9) 0.0321(4) Uani 1 1 d . . . . .
O1 O 0.96038(16) 0.54406(10) 0.64477(8) 0.0441(4) Uani 1 1 d . . . . .
O2 O 0.86937(17) 0.68836(11) 0.66973(9) 0.0508(4) Uani 1 1 d . . . . .
F1 F 0.4103(2) 0.99335(10) 0.57751(11) 0.0823(5) Uani 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'
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'
F F 0.0171 0.0103 '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
F1 C1 C2 118.07(19) . . ?
F1 C1 C6 118.5(2) . . ?
C2 C1 C6 123.4(2) . . ?
C1 C2 C3 117.49(19) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 120.59(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.10(16) . . ?
C4 C5 C7 120.59(16) . . ?
C6 C5 C7 121.06(17) . . ?
C1 C6 C5 119.10(19) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C11 108.45(15) . . ?
C8 C7 C5 129.50(17) . . ?
C11 C7 C5 121.80(16) . . ?
C7 C8 C18 127.27(16) . . ?
C7 C8 C9 106.93(16) . . ?
C18 C8 C9 125.16(16) . . ?
C20 C9 C10 120.96(16) . . ?
C20 C9 C8 131.54(16) . . ?
C10 C9 C8 106.68(15) . . ?
C11 C10 C9 107.43(16) . . ?
C11 C10 C12 125.75(16) . . ?
C9 C10 C12 126.79(16) . . ?
C10 C11 C7 110.33(16) . . ?
C10 C11 H11 124.8 . . ?
C7 C11 H11 124.8 . . ?
C13 C12 C17 117.71(18) . . ?
C13 C12 C10 120.29(16) . . ?
C17 C12 C10 121.95(17) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.98(19) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
O1 C18 O2 120.24(17) . . ?
O1 C18 C8 126.56(16) . . ?
O2 C18 C8 113.17(16) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C9 127.64(17) . . ?
N1 C20 H20 116.2 . . ?
C9 C20 H20 116.2 . . ?
C22 C21 C26 119.20(17) . . ?
C22 C21 N1 117.92(16) . . ?
C26 C21 N1 122.86(17) . . ?
C23 C22 C21 120.28(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.60(18) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.2(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 121.2(2) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 119.48(19) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C20 N1 C21 125.97(16) . . ?
C20 N1 H1N 117.7(13) . . ?
C21 N1 H1N 115.8(13) . . ?
C18 O2 C19 117.08(17) . . ?
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
C1 F1 1.358(3) . ?
C1 C2 1.359(4) . ?
C1 C6 1.372(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C7 1.482(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(3) . ?
C7 C11 1.412(3) . ?
C8 C18 1.448(3) . ?
C8 C9 1.461(3) . ?
C9 C20 1.382(3) . ?
C9 C10 1.447(3) . ?
C10 C11 1.375(3) . ?
C10 C12 1.473(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(3) . ?
C12 C17 1.398(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O1 1.229(2) . ?
C18 O2 1.334(2) . ?
C19 O2 1.443(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.331(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(3) . ?
C21 C26 1.387(3) . ?
C21 N1 1.416(2) . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1N 0.93(2) . ?
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 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C5 C7 -174.66(18) . . . . ?
F1 C1 C6 C5 179.33(19) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C7 C5 C6 C1 174.95(18) . . . . ?
C4 C5 C7 C8 -43.5(3) . . . . ?
C6 C5 C7 C8 142.3(2) . . . . ?
C4 C5 C7 C11 129.94(19) . . . . ?
C6 C5 C7 C11 -44.2(3) . . . . ?
C11 C7 C8 C18 167.44(16) . . . . ?
C5 C7 C8 C18 -18.4(3) . . . . ?
C11 C7 C8 C9 -3.67(19) . . . . ?
C5 C7 C8 C9 170.50(17) . . . . ?
C7 C8 C9 C20 -164.94(18) . . . . ?
C18 C8 C9 C20 23.7(3) . . . . ?
C7 C8 C9 C10 4.46(18) . . . . ?
C18 C8 C9 C10 -166.89(16) . . . . ?
C20 C9 C10 C11 167.16(16) . . . . ?
C8 C9 C10 C11 -3.60(18) . . . . ?
C20 C9 C10 C12 -14.6(3) . . . . ?
C8 C9 C10 C12 174.60(16) . . . . ?
C9 C10 C11 C7 1.40(19) . . . . ?
C12 C10 C11 C7 -176.81(16) . . . . ?
C8 C7 C11 C10 1.5(2) . . . . ?
C5 C7 C11 C10 -173.24(15) . . . . ?
C11 C10 C12 C13 -36.1(3) . . . . ?
C9 C10 C12 C13 145.99(18) . . . . ?
C11 C10 C12 C17 141.34(19) . . . . ?
C9 C10 C12 C17 -36.5(3) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C10 C12 C13 C14 179.44(18) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -1.7(4) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C12 1.2(3) . . . . ?
C13 C12 C17 C16 -2.6(3) . . . . ?
C10 C12 C17 C16 179.87(17) . . . . ?
C7 C8 C18 O1 175.83(18) . . . . ?
C9 C8 C18 O1 -14.6(3) . . . . ?
C7 C8 C18 O2 -6.3(3) . . . . ?
C9 C8 C18 O2 163.33(16) . . . . ?
C10 C9 C20 N1 -176.78(16) . . . . ?
C8 C9 C20 N1 -8.6(3) . . . . ?
C26 C21 C22 C23 1.2(3) . . . . ?
N1 C21 C22 C23 -177.42(15) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 C26 1.3(4) . . . . ?
C24 C25 C26 C21 -0.6(4) . . . . ?
C22 C21 C26 C25 -0.6(3) . . . . ?
N1 C21 C26 C25 177.9(2) . . . . ?
C9 C20 N1 C21 179.85(17) . . . . ?
C22 C21 N1 C20 165.08(16) . . . . ?
C26 C21 N1 C20 -13.5(3) . . . . ?
O1 C18 O2 C19 -1.4(3) . . . . ?
C8 C18 O2 C19 -179.4(2) . . . . ?
