#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:29:15 +0100 (Sun 04 de Feb de 2024) $
#$Revision: 289626 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/97/7159734.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_7159734
loop_
_publ_author_name
'Shahid, M.'
'Muthuraja, Perumal'
'Gopinath, Purushothaman'
_publ_section_title
;
 Substituent-controlled regioselective arylation of carbazoles using dual
 catalysis.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              753
_journal_page_last               758
_journal_paper_doi               10.1039/d3ob01827j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H17 N3 O'
_chemical_formula_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.39
_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
_audit_creation_date             2023-04-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-06-06 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.192(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3575(5)
_cell_length_b                   19.3150(15)
_cell_length_c                   12.3105(9)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      2.69
_cell_volume                     1735.7(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            95588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.045
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         2.109
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1366 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.9212.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0369
_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)+(0.0500P)²+0.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2476
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01827j2.cif
_cod_data_source_block           mo_sk_111_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159731--7159734.cif.'
_cod_database_code               7159734
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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
O2 O 0.59503(16) 0.46663(6) 0.32947(11) 0.0528(3) Uani 1 1 d . . . . .
N1 N 0.19125(16) 0.64883(6) 0.33489(9) 0.0328(3) Uani 1 1 d . . . . .
N2 N -0.01865(17) 0.73844(6) 0.29983(10) 0.0355(3) Uani 1 1 d . . . . .
N3 N 0.10400(16) 0.70969(6) 0.48294(9) 0.0329(3) Uani 1 1 d . . . . .
C1 C 0.47999(19) 0.74062(8) 0.47761(12) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.5165(2) 0.76163(10) 0.58622(13) 0.0458(4) Uani 1 1 d . . . . .
H2 H 0.556299 0.728561 0.641213 0.055 Uiso 1 1 calc R U . . .
C3 C 0.4955(2) 0.82995(11) 0.61507(15) 0.0550(5) Uani 1 1 d . . . . .
H3 H 0.519295 0.843385 0.689732 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4403(2) 0.87880(10) 0.53611(16) 0.0542(5) Uani 1 1 d . . . . .
H4 H 0.424785 0.925662 0.556515 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4077(2) 0.85962(9) 0.42751(15) 0.0460(4) Uani 1 1 d . . . . .
H5 H 0.372218 0.893318 0.372729 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4271(2) 0.79077(8) 0.39876(13) 0.0376(4) Uani 1 1 d . . . . .
H6 H 0.403754 0.777643 0.323939 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5007(2) 0.66714(8) 0.44711(12) 0.0370(4) Uani 1 1 d . . . . .
C8 C 0.3688(2) 0.62912(8) 0.37966(12) 0.0342(3) Uani 1 1 d . . . . .
C9 C 0.4031(2) 0.56260(8) 0.34028(12) 0.0373(4) Uani 1 1 d . . . . .
C10 C 0.5717(2) 0.53061(8) 0.37318(14) 0.0425(4) Uani 1 1 d . . . . .
C11 C 0.6991(2) 0.56488(9) 0.44488(14) 0.0481(4) Uani 1 1 d . . . . .
H11 H 0.812103 0.543085 0.470602 0.058 Uiso 1 1 calc R U . . .
C12 C 0.6629(2) 0.63165(9) 0.48001(14) 0.0442(4) Uani 1 1 d . . . . .
H12 H 0.754154 0.654116 0.529119 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1152(2) 0.59541(7) 0.26592(12) 0.0340(3) Uani 1 1 d . . . . .
C14 C 0.2433(2) 0.54135(8) 0.26765(12) 0.0374(4) Uani 1 1 d . . . . .
C15 C 0.08611(19) 0.70205(7) 0.37493(11) 0.0302(3) Uani 1 1 d . . . . .
C16 C -0.1134(2) 0.78955(8) 0.33973(13) 0.0371(4) Uani 1 1 d . . . . .
H16 H -0.193232 0.816568 0.289951 0.044 Uiso 1 1 calc R U . . .
C17 C -0.1007(2) 0.80476(8) 0.44944(12) 0.0358(4) Uani 1 1 d . . . . .
H17 H -0.165928 0.842324 0.475911 0.043 Uiso 1 1 calc R U . . .
C18 C 0.0115(2) 0.76281(8) 0.51907(12) 0.0344(3) Uani 1 1 d . . . . .
H18 H 0.023645 0.771912 0.595469 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7620(3) 0.43098(10) 0.36758(16) 0.0623(6) Uani 1 1 d . . . . .
H19A H 0.757412 0.383982 0.337359 0.093 Uiso 1 1 calc R U . . .
H19B H 0.776625 0.428620 0.447720 0.093 Uiso 1 1 calc R U . . .
H19C H 0.865859 0.455980 0.343686 0.093 Uiso 1 1 calc R U . . .
C20 C -0.0560(2) 0.59149(8) 0.20561(12) 0.0389(4) Uani 1 1 d . . . . .
H20 H -0.142370 0.627981 0.206701 0.047 Uiso 1 1 calc R U . . .
C21 C -0.0972(2) 0.53260(8) 0.14367(13) 0.0441(4) Uani 1 1 d . . . . .
H21 H -0.213498 0.528755 0.100905 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0284(3) 0.47879(9) 0.14270(14) 0.0476(4) Uani 1 1 d . . . . .
H22 H -0.003324 0.438987 0.099077 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1979(2) 0.48237(8) 0.20392(14) 0.0451(4) Uani 1 1 d . . . . .
H23 H 0.282737 0.445371 0.202987 0.054 Uiso 1 1 calc R U . . .
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'
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
C10 O2 C19 116.73(15) . . ?
C8 N1 C13 108.53(12) . . ?
C8 N1 C15 125.69(12) . . ?
C13 N1 C15 123.41(12) . . ?
C15 N2 C16 114.77(12) . . ?
C15 N3 C18 115.30(12) . . ?
C2 C1 C6 118.08(15) . . ?
C2 C1 C7 120.66(15) . . ?
C6 C1 C7 121.25(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.80(17) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.36(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.98(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.58(17) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.17(15) . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C1 124.48(13) . . ?
C12 C7 C1 120.65(15) . . ?
C12 C7 C8 114.77(15) . . ?
N1 C8 C9 108.09(13) . . ?
C7 C8 N1 129.08(14) . . ?
C7 C8 C9 122.75(14) . . ?
C8 C9 C14 107.78(13) . . ?
C10 C9 C8 119.62(15) . . ?
C10 C9 C14 132.59(15) . . ?
O2 C10 C9 115.83(15) . . ?
O2 C10 C11 125.36(15) . . ?
C11 C10 C9 118.81(15) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.16(15) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 123.67(16) . . ?
C7 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C14 C13 N1 108.68(13) . . ?
C20 C13 N1 129.15(13) . . ?
C20 C13 C14 122.15(14) . . ?
C13 C14 C9 106.90(13) . . ?
C23 C14 C9 134.19(15) . . ?
C23 C14 C13 118.91(15) . . ?
N2 C15 N1 115.96(12) . . ?
N3 C15 N1 116.14(12) . . ?
N3 C15 N2 127.90(13) . . ?
N2 C16 H16 118.5 . . ?
N2 C16 C17 122.98(14) . . ?
C17 C16 H16 118.5 . . ?
C16 C17 H17 121.7 . . ?
C16 C17 C18 116.63(14) . . ?
C18 C17 H17 121.7 . . ?
N3 C18 C17 122.32(13) . . ?
N3 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20 121.2 . . ?
C21 C20 C13 117.61(15) . . ?
C21 C20 H20 121.2 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.32(16) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.99(16) . . ?
C23 C22 H22 119.5 . . ?
C14 C23 H23 120.5 . . ?
C22 C23 C14 118.99(15) . . ?
C22 C23 H23 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
O2 C10 1.367(2) . ?
O2 C19 1.435(2) . ?
N1 C8 1.4051(19) . ?
N1 C13 1.4071(19) . ?
N1 C15 1.4118(18) . ?
N2 C15 1.3283(19) . ?
N2 C16 1.3372(19) . ?
N3 C15 1.3279(18) . ?
N3 C18 1.3378(19) . ?
C1 C2 1.391(2) . ?
C1 C6 1.392(2) . ?
C1 C7 1.481(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(2) . ?
C7 C12 1.392(2) . ?
C8 C9 1.407(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.445(2) . ?
C10 C11 1.375(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(2) . ?
C13 C20 1.382(2) . ?
C14 C23 1.400(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.382(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.392(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.375(3) . ?
C23 H23 0.9500 . ?
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
O2 C10 C11 C12 176.91(14) . . . . ?
N1 C8 C9 C10 -179.73(13) . . . . ?
N1 C8 C9 C14 1.06(15) . . . . ?
N1 C13 C14 C9 0.01(15) . . . . ?
N1 C13 C14 C23 -179.53(13) . . . . ?
N1 C13 C20 C21 179.93(14) . . . . ?
N2 C16 C17 C18 -2.2(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C1 C7 C8 N1 -5.2(2) . . . . ?
C1 C7 C8 C9 171.01(13) . . . . ?
C1 C7 C12 C11 -173.05(14) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C2 C1 C7 C8 131.39(16) . . . . ?
C2 C1 C7 C12 -52.4(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C6 C1 C7 C8 -49.8(2) . . . . ?
C6 C1 C7 C12 126.35(16) . . . . ?
C7 C1 C2 C3 -179.34(14) . . . . ?
C7 C1 C6 C5 180.00(14) . . . . ?
C7 C8 C9 C10 3.3(2) . . . . ?
C7 C8 C9 C14 -175.87(13) . . . . ?
C8 N1 C13 C14 0.65(15) . . . . ?
C8 N1 C13 C20 179.28(14) . . . . ?
C8 N1 C15 N2 144.01(14) . . . . ?
C8 N1 C15 N3 -35.94(19) . . . . ?
C8 C7 C12 C11 3.5(2) . . . . ?
C8 C9 C10 O2 -178.78(12) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C8 C9 C14 C13 -0.66(16) . . . . ?
C8 C9 C14 C23 178.77(16) . . . . ?
C9 C10 C11 C12 -2.8(2) . . . . ?
C9 C14 C23 C22 179.82(16) . . . . ?
C10 C9 C14 C13 -179.73(15) . . . . ?
C10 C9 C14 C23 -0.3(3) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C12 C7 C8 N1 178.40(14) . . . . ?
C12 C7 C8 C9 -5.4(2) . . . . ?
C13 N1 C8 C7 175.61(14) . . . . ?
C13 N1 C8 C9 -1.06(15) . . . . ?
C13 N1 C15 N2 -55.48(18) . . . . ?
C13 N1 C15 N3 124.57(14) . . . . ?
C13 C14 C23 C22 -0.8(2) . . . . ?
C13 C20 C21 C22 0.6(2) . . . . ?
C14 C9 C10 O2 0.2(2) . . . . ?
C14 C9 C10 C11 179.92(15) . . . . ?
C14 C13 C20 C21 -1.6(2) . . . . ?
C15 N1 C8 C7 -21.5(2) . . . . ?
C15 N1 C8 C9 161.86(12) . . . . ?
C15 N1 C13 C14 -162.75(12) . . . . ?
C15 N1 C13 C20 15.9(2) . . . . ?
C15 N2 C16 C17 1.6(2) . . . . ?
C15 N3 C18 C17 2.7(2) . . . . ?
C16 N2 C15 N1 -178.48(12) . . . . ?
C16 N2 C15 N3 1.5(2) . . . . ?
C16 C17 C18 N3 -0.1(2) . . . . ?
C18 N3 C15 N1 176.35(12) . . . . ?
C18 N3 C15 N2 -3.6(2) . . . . ?
C19 O2 C10 C9 -176.04(14) . . . . ?
C19 O2 C10 C11 4.3(2) . . . . ?
C20 C13 C14 C9 -178.73(13) . . . . ?
C20 C13 C14 C23 1.7(2) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C14 -0.2(2) . . . . ?
