#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:58:16 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159897.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_7159897
loop_
_publ_author_name
'Yaragorla, Srinivasarao'
'Khan, Tabassum'
'Chakroborty, Sayonika'
_publ_section_title
;
 Cu(OTf)₂/HFIP catalyzed regioselective cycloisomerization of
 indole-C3-functionalized alkynols to carbazoles.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3622
_journal_page_last               3629
_journal_paper_doi               10.1039/d4ob00421c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C37 H27 N'
_chemical_formula_sum            'C37 H27 N'
_chemical_formula_weight         485.59
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                66.465(4)
_cell_angle_beta                 77.764(5)
_cell_angle_gamma                82.339(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6614(12)
_cell_length_b                   12.3016(17)
_cell_length_c                   12.4047(16)
_cell_measurement_reflns_used    7342
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.70
_cell_measurement_theta_min      2.57
_cell_volume                     1319.0(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.2231
_diffrn_reflns_Laue_measured_fraction_full 0.891
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20603
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.808
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1798 before and 0.1053 after correction.
The Ratio of minimum to maximum transmission is 0.8163.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.1040
_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)+(0.0752P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2546
_refine_ls_wR_factor_ref         0.2919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2010
_reflns_number_total             4319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00421c2.cif
_cod_data_source_block           ysr014_0m
_cod_depositor_comments
'Adding full bibliography for 7159896--7159898.cif.'
_cod_database_code               7159897
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_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:
 C5(H5), C12(H12), C11(H11), C26(H26), C23(H23), C9(H9), C29(H29), C27(H27),
 C8(H8), C36(H36), C10(H10), C30(H30), C14(H14), C35(H35), C20(H20), C15(H15),
 C16(H16), C18(H18), C21(H21), C34(H34), C22(H22), C32(H32), C17(H17), C33(H33)
2.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
N1 N 0.1087(4) 0.1270(4) 0.7335(4) 0.0656(11) Uani 1 1 d . . . . .
C2 C 0.1771(4) 0.1148(4) 0.6274(4) 0.0510(10) Uani 1 1 d . . . . .
C5 C 0.3138(4) 0.1386(4) 0.4027(4) 0.0497(10) Uani 1 1 d . . . . .
H5 H 0.359255 0.145234 0.326505 0.060 Uiso 1 1 calc R . . . .
C25 C 0.3571(4) 0.3513(4) 0.3406(4) 0.0514(10) Uani 1 1 d . . . . .
C6 C 0.2677(4) 0.0290(4) 0.4827(4) 0.0477(10) Uani 1 1 d . . . . .
C1 C 0.2010(4) 0.0129(4) 0.5997(4) 0.0511(10) Uani 1 1 d . . . . .
C4 C 0.2964(4) 0.2396(4) 0.4292(4) 0.0492(10) Uani 1 1 d . . . . .
C7 C 0.2911(4) -0.0708(4) 0.4407(4) 0.0507(10) Uani 1 1 d . . . . .
C19 C 0.1729(4) 0.3128(4) 0.5985(4) 0.0543(11) Uani 1 1 d . . . . .
C12 C 0.4258(5) -0.0991(4) 0.3874(4) 0.0573(11) Uani 1 1 d . . . . .
H12 H 0.503470 -0.060568 0.385404 0.069 Uiso 1 1 calc R . . . .
C3 C 0.2219(4) 0.2272(4) 0.5432(4) 0.0497(10) Uani 1 1 d . . . . .
C11 C 0.4447(6) -0.1829(4) 0.3381(5) 0.0711(14) Uani 1 1 d . . . . .
H11 H 0.534641 -0.200034 0.301686 0.085 Uiso 1 1 calc R . . . .
C26 C 0.4551(5) 0.4070(4) 0.3653(4) 0.0616(12) Uani 1 1 d . . . . .
H26 H 0.482732 0.373855 0.439781 0.074 Uiso 1 1 calc R . . . .
C24 C 0.1022(4) 0.2467(5) 0.7150(5) 0.0642(13) Uani 1 1 d . . . . .
C31 C 0.5279(5) 0.6808(4) 0.0836(4) 0.0568(11) Uani 1 1 d . . . . .
C13 C 0.1666(4) -0.1083(4) 0.6892(4) 0.0538(11) Uani 1 1 d . . . . .
C23 C 0.0299(6) 0.2999(5) 0.7944(5) 0.0783(15) Uani 1 1 d . . . . .
H23 H -0.019044 0.255373 0.869442 0.094 Uiso 1 1 calc R . . . .
C9 C 0.1976(6) -0.2172(4) 0.3972(5) 0.0713(14) Uani 1 1 d . . . . .
H9 H 0.120810 -0.258055 0.401723 0.086 Uiso 1 1 calc R . . . .
C28 C 0.4743(4) 0.5653(4) 0.1699(4) 0.0531(10) Uani 1 1 d . . . . .
C29 C 0.3792(5) 0.5067(5) 0.1449(4) 0.0701(14) Uani 1 1 d . . . . .
H29 H 0.352019 0.539355 0.070347 0.084 Uiso 1 1 calc R . . . .
C27 C 0.5119(4) 0.5104(4) 0.2817(4) 0.0598(12) Uani 1 1 d . . . . .
H27 H 0.578164 0.544770 0.301031 0.072 Uiso 1 1 calc R . . . .
C8 C 0.1787(5) -0.1323(4) 0.4451(4) 0.0600(12) Uani 1 1 d . . . . .
H8 H 0.088396 -0.115574 0.481388 0.072 Uiso 1 1 calc R . . . .
C36 C 0.4440(6) 0.7650(5) 0.0074(5) 0.0789(15) Uani 1 1 d . . . . .
H36 H 0.352703 0.746719 0.009975 0.095 Uiso 1 1 calc R . . . .
C10 C 0.3303(7) -0.2419(5) 0.3425(5) 0.0793(16) Uani 1 1 d . . . . .
H10 H 0.343112 -0.298339 0.308489 0.095 Uiso 1 1 calc R . . . .
C30 C 0.3249(5) 0.4028(4) 0.2268(4) 0.0680(13) Uani 1 1 d . . . . .
H30 H 0.264118 0.365341 0.205313 0.082 Uiso 1 1 calc R . . . .
C14 C 0.2754(5) -0.1882(5) 0.7329(4) 0.0675(12) Uani 1 1 d . . . . .
H14 H 0.368114 -0.164489 0.705826 0.081 Uiso 1 1 calc R . . . .
C35 C 0.4912(7) 0.8739(5) -0.0713(6) 0.0897(17) Uani 1 1 d . . . . .
H35 H 0.432355 0.928002 -0.120927 0.108 Uiso 1 1 calc R . . . .
C20 C 0.1730(5) 0.4341(5) 0.5629(5) 0.0733(14) Uani 1 1 d . . . . .
H20 H 0.216425 0.481048 0.486584 0.088 Uiso 1 1 calc R . . . .
C15 C 0.2516(7) -0.3003(5) 0.8141(5) 0.0821(15) Uani 1 1 d . . . . .
H15 H 0.327769 -0.351308 0.841822 0.098 Uiso 1 1 calc R . . . .
C16 C 0.1193(9) -0.3384(6) 0.8548(6) 0.0954(19) Uani 1 1 d . . . . .
H16 H 0.103723 -0.415327 0.910045 0.115 Uiso 1 1 calc R . . . .
C18 C 0.0298(5) -0.1467(5) 0.7308(5) 0.0846(17) Uani 1 1 d . . . . .
H18 H -0.046847 -0.096023 0.703606 0.102 Uiso 1 1 calc R . . . .
C21 C 0.1061(6) 0.4845(6) 0.6448(6) 0.0895(17) Uani 1 1 d . . . . .
H21 H 0.109595 0.565803 0.623259 0.107 Uiso 1 1 calc R . . . .
C34 C 0.6253(7) 0.9022(6) -0.0764(6) 0.0905(17) Uani 1 1 d . . . . .
H34 H 0.658880 0.975310 -0.130060 0.109 Uiso 1 1 calc R . . . .
C22 C 0.0353(7) 0.4180(6) 0.7562(6) 0.0930(18) Uani 1 1 d . . . . .
H22 H -0.010215 0.456088 0.806478 0.112 Uiso 1 1 calc R . . . .
C32 C 0.6612(6) 0.7124(5) 0.0745(5) 0.0848(16) Uani 1 1 d . . . . .
H32 H 0.722115 0.657826 0.121653 0.102 Uiso 1 1 calc R . . . .
C17 C 0.0083(7) -0.2630(6) 0.8142(6) 0.103(2) Uani 1 1 d . . . . .
H17 H -0.083412 -0.289057 0.842384 0.124 Uiso 1 1 calc R . . . .
C33 C 0.7088(7) 0.8224(6) -0.0022(7) 0.103(2) Uani 1 1 d . . . . .
H33 H 0.798741 0.842111 -0.003065 0.123 Uiso 1 1 calc R . . . .
C37 C 0.0448(9) 0.0401(7) 0.8437(6) 0.122(3) Uani 1 1 d . . . . .
H37A H -0.020473 -0.002246 0.828396 0.184 Uiso 1 1 calc GR . . . .
H37B H -0.005221 0.078801 0.895341 0.184 Uiso 1 1 calc GR . . . .
H37C H 0.117075 -0.014649 0.881392 0.184 Uiso 1 1 calc GR . . . .
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'
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
C2 N1 C37 130.1(4) . . ?
C24 N1 C2 108.1(4) . . ?
C24 N1 C37 121.8(4) . . ?
N1 C2 C1 129.3(4) . . ?
N1 C2 C3 108.8(3) . . ?
C1 C2 C3 122.0(4) . . ?
C6 C5 C4 123.9(4) . . ?
C26 C25 C4 121.6(4) . . ?
C30 C25 C4 121.9(3) . . ?
C30 C25 C26 116.5(4) . . ?
C5 C6 C1 120.7(4) . . ?
C5 C6 C7 117.9(4) . . ?
C1 C6 C7 121.4(4) . . ?
C2 C1 C13 123.2(4) . . ?
C6 C1 C2 116.4(4) . . ?
C6 C1 C13 120.2(4) . . ?
C5 C4 C25 120.1(4) . . ?
C5 C4 C3 116.3(4) . . ?
C3 C4 C25 123.5(3) . . ?
C12 C7 C6 120.7(3) . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 C12 118.1(4) . . ?
C24 C19 C3 105.6(4) . . ?
C20 C19 C3 136.1(5) . . ?
C20 C19 C24 118.2(4) . . ?
C11 C12 C7 120.7(4) . . ?
C2 C3 C19 107.4(4) . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 C19 132.1(4) . . ?
C12 C11 C10 120.1(5) . . ?
C27 C26 C25 121.0(4) . . ?
N1 C24 C19 110.0(4) . . ?
N1 C24 C23 126.9(5) . . ?
C23 C24 C19 122.9(5) . . ?
C36 C31 C28 121.7(4) . . ?
C32 C31 C28 122.3(5) . . ?
C32 C31 C36 116.0(5) . . ?
C14 C13 C1 119.2(4) . . ?
C14 C13 C18 117.4(5) . . ?
C18 C13 C1 123.4(4) . . ?
C22 C23 C24 116.5(6) . . ?
C8 C9 C10 119.8(4) . . ?
C29 C28 C31 121.9(4) . . ?
C27 C28 C31 122.2(3) . . ?
C27 C28 C29 115.8(4) . . ?
C30 C29 C28 121.8(4) . . ?
C26 C27 C28 122.5(4) . . ?
C9 C8 C7 121.4(5) . . ?
C35 C36 C31 122.4(5) . . ?
C9 C10 C11 120.0(4) . . ?
C29 C30 C25 122.2(4) . . ?
C15 C14 C13 122.3(5) . . ?
C34 C35 C36 119.6(6) . . ?
C19 C20 C21 118.0(5) . . ?
C16 C15 C14 120.7(6) . . ?
C15 C16 C17 119.3(6) . . ?
C13 C18 C17 119.1(6) . . ?
C22 C21 C20 122.3(6) . . ?
C33 C34 C35 119.2(6) . . ?
C23 C22 C21 122.0(5) . . ?
C31 C32 C33 122.2(6) . . ?
C16 C17 C18 121.2(5) . . ?
C34 C33 C32 120.6(6) . . ?
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
N1 C2 1.397(5) . ?
N1 C24 1.392(6) . ?
N1 C37 1.430(8) . ?
C2 C1 1.406(6) . ?
C2 C3 1.416(6) . ?
C5 C6 1.380(6) . ?
C5 C4 1.388(5) . ?
C25 C4 1.475(6) . ?
C25 C26 1.387(5) . ?
C25 C30 1.382(6) . ?
C6 C1 1.403(6) . ?
C6 C7 1.489(6) . ?
C1 C13 1.490(6) . ?
C4 C3 1.402(6) . ?
C7 C12 1.396(6) . ?
C7 C8 1.384(6) . ?
C19 C3 1.452(6) . ?
C19 C24 1.417(7) . ?
C19 C20 1.376(7) . ?
C12 C11 1.370(6) . ?
C11 C10 1.382(8) . ?
C26 C27 1.373(7) . ?
C24 C23 1.410(7) . ?
C31 C28 1.477(6) . ?
C31 C36 1.393(7) . ?
C31 C32 1.364(7) . ?
C13 C14 1.380(7) . ?
C13 C18 1.386(6) . ?
C23 C22 1.341(9) . ?
C9 C8 1.370(6) . ?
C9 C10 1.374(8) . ?
C28 C29 1.390(6) . ?
C28 C27 1.383(6) . ?
C29 C30 1.362(7) . ?
C36 C35 1.373(8) . ?
C14 C15 1.359(7) . ?
C35 C34 1.369(8) . ?
C20 C21 1.398(7) . ?
C15 C16 1.343(9) . ?
C16 C17 1.362(9) . ?
C18 C17 1.402(9) . ?
C21 C22 1.376(10) . ?
C34 C33 1.358(9) . ?
C32 C33 1.378(8) . ?
