#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/40/7154036.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_7154036
loop_
_publ_author_name
'Rathore, Kuldeep Singh'
'Harode, Mandeep'
'Katukojvala, Sreenivas'
_publ_section_title
;
 Regioselective π-extension of indoles with rhodium enalcarbenoids -
 synthesis of substituted carbazoles.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8641
_journal_page_last               8645
_journal_paper_doi               10.1039/c4ob01693a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.295(3)
_cell_length_b                   7.7566(16)
_cell_length_c                   33.943(8)
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.93
_cell_measurement_theta_min      2.92
_cell_volume                     3237.1(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_sigmaI/netI    0.1161
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            5311
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                1433
_reflns_number_total             2781
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01693a4.cif
_cod_data_source_block           R7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7154036--7154038.cif.

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        3237.0(13)
_cod_database_code               7154036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.7007(2) -0.1642(3) 0.71436(7) 0.0394(7) Uani 1 1 d .
H1 H 0.7453 -0.2003 0.7329 0.047 Uiso 1 1 calc R
O1 O 0.25853(17) -0.2259(3) 0.69936(5) 0.0415(6) Uani 1 1 d .
O2 O 0.46964(16) 0.1476(3) 0.61121(5) 0.0405(6) Uani 1 1 d .
O3 O 0.59217(15) 0.1602(2) 0.56237(5) 0.0338(5) Uani 1 1 d .
C1 C 0.5888(3) -0.1858(4) 0.71451(8) 0.0326(8) Uani 1 1 d .
C2 C 0.5454(2) -0.1028(3) 0.68112(8) 0.0271(7) Uani 1 1 d .
C3 C 0.4311(2) -0.1108(4) 0.67508(8) 0.0299(7) Uani 1 1 d .
H3 H 0.3975 -0.0528 0.6536 0.036 Uiso 1 1 calc R
C4 C 0.3711(2) -0.2056(4) 0.70143(8) 0.0349(8) Uani 1 1 d .
C5 C 0.4180(3) -0.2920(4) 0.73327(8) 0.0382(8) Uani 1 1 d .
H5 H 0.3732 -0.3591 0.7502 0.046 Uiso 1 1 calc R
C6 C 0.5267(3) -0.2819(4) 0.74054(8) 0.0398(8) Uani 1 1 d .
H6 H 0.5586 -0.3383 0.7625 0.048 Uiso 1 1 calc R
C7 C 0.6369(2) -0.0320(4) 0.65947(7) 0.0269(7) Uani 1 1 d .
C8 C 0.7307(2) -0.0783(4) 0.68097(8) 0.0309(8) Uani 1 1 d .
C9 C 0.8376(2) -0.0452(4) 0.66852(9) 0.0399(8) Uani 1 1 d .
H9 H 0.8985 -0.0767 0.6842 0.048 Uiso 1 1 calc R
C10 C 0.8501(2) 0.0344(4) 0.63291(9) 0.0391(8) Uani 1 1 d .
H10 H 0.9213 0.0555 0.6232 0.047 Uiso 1 1 calc R
C11 C 0.7602(2) 0.0854(4) 0.61051(8) 0.0348(8) Uani 1 1 d .
H11 H 0.7716 0.1432 0.5862 0.042 Uiso 1 1 calc R
C12 C 0.6535(2) 0.0530(4) 0.62318(8) 0.0285(7) Uani 1 1 d .
C13 C 0.2025(2) -0.1442(4) 0.66712(8) 0.0379(8) Uani 1 1 d .
H13A H 0.2142 -0.0193 0.6683 0.057 Uiso 1 1 calc R
H13B H 0.1245 -0.1687 0.6690 0.057 Uiso 1 1 calc R
H13C H 0.2307 -0.1888 0.6421 0.057 Uiso 1 1 calc R
C14 C 0.5616(3) 0.1233(4) 0.59964(8) 0.0311(8) Uani 1 1 d .
C15 C 0.5128(2) 0.2505(4) 0.53835(8) 0.0348(8) Uani 1 1 d .
H15A H 0.4873 0.3557 0.5520 0.042 Uiso 1 1 calc R
H15B H 0.4493 0.1755 0.5331 0.042 Uiso 1 1 calc R
C16 C 0.5682(2) 0.2966(3) 0.50083(8) 0.0278(7) Uani 1 1 d .
C17 C 0.6621(2) 0.4008(4) 0.50161(9) 0.0358(8) Uani 1 1 d .
H17 H 0.6892 0.4410 0.5262 0.043 Uiso 1 1 calc R
C18 C 0.7152(3) 0.4453(4) 0.46738(11) 0.0491(9) Uani 1 1 d .
H18 H 0.7778 0.5169 0.4683 0.059 Uiso 1 1 calc R
C19 C 0.6767(3) 0.3849(5) 0.43163(10) 0.0567(11) Uani 1 1 d .
H19 H 0.7140 0.4134 0.4080 0.068 Uiso 1 1 calc R
C20 C 0.5860(3) 0.2852(5) 0.43016(9) 0.0520(10) Uani 1 1 d .
H20 H 0.5599 0.2453 0.4054 0.062 Uiso 1 1 calc R
C21 C 0.5303(3) 0.2404(4) 0.46480(9) 0.0391(8) Uani 1 1 d .
H21 H 0.4665 0.1714 0.4634 0.047 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'
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
C8 N1 C1 109.3(2)
C8 N1 H1 125.3
C1 N1 H1 125.3
C4 O1 C13 117.6(2)
C14 O3 C15 116.2(2)
C6 C1 N1 127.9(3)
C6 C1 C2 123.4(3)
N1 C1 C2 108.5(3)
C1 C2 C3 118.1(3)
C1 C2 C7 106.7(2)
C3 C2 C7 135.2(3)
C4 C3 C2 117.4(3)
C4 C3 H3 121.3
C2 C3 H3 121.3
C3 C4 O1 124.1(3)
C3 C4 C5 122.7(3)
O1 C4 C5 113.2(3)
C6 C5 C4 121.2(3)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 117.2(3)
C5 C6 H6 121.4
C1 C6 H6 121.4
C8 C7 C12 116.8(3)
C8 C7 C2 106.0(2)
C12 C7 C2 137.0(3)
N1 C8 C9 126.3(3)
N1 C8 C7 109.4(3)
C9 C8 C7 124.3(3)
C10 C9 C8 117.0(3)
C10 C9 H9 121.5
C8 C9 H9 121.5
C9 C10 C11 121.3(3)
C9 C10 H10 119.3
C11 C10 H10 119.3
C10 C11 C12 121.4(3)
C10 C11 H11 119.3
C12 C11 H11 119.3
C11 C12 C7 119.1(3)
C11 C12 C14 118.7(3)
C7 C12 C14 122.0(3)
O1 C13 H13A 109.5
O1 C13 H13B 109.5
H13A C13 H13B 109.5
O1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O2 C14 O3 122.0(3)
O2 C14 C12 126.3(3)
O3 C14 C12 111.7(3)
O3 C15 C16 106.8(2)
O3 C15 H15A 110.4
C16 C15 H15A 110.4
O3 C15 H15B 110.4
C16 C15 H15B 110.4
H15A C15 H15B 108.6
C21 C16 C17 118.4(3)
C21 C16 C15 121.9(3)
C17 C16 C15 119.8(3)
C18 C17 C16 121.1(3)
C18 C17 H17 119.5
C16 C17 H17 119.5
C17 C18 C19 119.6(3)
C17 C18 H18 120.2
C19 C18 H18 120.2
C20 C19 C18 120.4(3)
C20 C19 H19 119.8
C18 C19 H19 119.8
C19 C20 C21 120.7(3)
C19 C20 H20 119.6
C21 C20 H20 119.6
C16 C21 C20 119.9(3)
C16 C21 H21 120.0
C20 C21 H21 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.366(3)
N1 C1 1.385(4)
N1 H1 0.8800
O1 C4 1.395(3)
O1 C13 1.441(3)
O2 C14 1.212(3)
O3 C14 1.351(3)
O3 C15 1.451(3)
C1 C6 1.385(4)
C1 C2 1.409(4)
C2 C3 1.422(4)
C2 C7 1.451(4)
C3 C4 1.373(4)
C3 H3 0.9500
C4 C5 1.396(4)
C5 C6 1.361(4)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.412(4)
C7 C12 1.412(4)
C8 C9 1.404(4)
C9 C10 1.366(4)
C9 H9 0.9500
C10 C11 1.399(4)
C10 H10 0.9500
C11 C12 1.403(4)
C11 H11 0.9500
C12 C14 1.488(4)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C15 C16 1.488(4)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C21 1.380(4)
C16 C17 1.409(4)
C17 C18 1.376(4)
C17 H17 0.9500
C18 C19 1.384(5)
C18 H18 0.9500
C19 C20 1.358(5)
C19 H19 0.9500
C20 C21 1.404(4)
C20 H20 0.9500
C21 H21 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
C8 N1 C1 C6 172.3(3)
C8 N1 C1 C2 -3.2(3)
C6 C1 C2 C3 3.4(4)
N1 C1 C2 C3 179.1(2)
C6 C1 C2 C7 -174.2(3)
N1 C1 C2 C7 1.6(3)
C1 C2 C3 C4 -2.7(4)
C7 C2 C3 C4 174.0(3)
C2 C3 C4 O1 -179.8(2)
C2 C3 C4 C5 0.1(4)
C13 O1 C4 C3 1.0(4)
C13 O1 C4 C5 -179.0(2)
C3 C4 C5 C6 2.1(5)
O1 C4 C5 C6 -177.9(3)
C4 C5 C6 C1 -1.5(4)
N1 C1 C6 C5 -176.1(3)
C2 C1 C6 C5 -1.3(4)
C1 C2 C7 C8 0.6(3)
C3 C2 C7 C8 -176.4(3)
C1 C2 C7 C12 174.4(3)
C3 C2 C7 C12 -2.5(6)
C1 N1 C8 C9 -174.1(3)
C1 N1 C8 C7 3.6(3)
C12 C7 C8 N1 -177.8(2)
C2 C7 C8 N1 -2.6(3)
C12 C7 C8 C9 0.0(4)
C2 C7 C8 C9 175.3(3)
N1 C8 C9 C10 176.3(3)
C7 C8 C9 C10 -1.2(4)
C8 C9 C10 C11 2.0(4)
C9 C10 C11 C12 -1.7(4)
C10 C11 C12 C7 0.4(4)
C10 C11 C12 C14 175.0(3)
C8 C7 C12 C11 0.4(4)
C2 C7 C12 C11 -172.9(3)
C8 C7 C12 C14 -174.0(2)
C2 C7 C12 C14 12.6(5)
C15 O3 C14 O2 7.4(4)
C15 O3 C14 C12 -172.2(2)
C11 C12 C14 O2 -158.9(3)
C7 C12 C14 O2 15.6(5)
C11 C12 C14 O3 20.7(4)
C7 C12 C14 O3 -164.9(2)
C14 O3 C15 C16 173.0(2)
O3 C15 C16 C21 121.1(3)
O3 C15 C16 C17 -59.0(3)
C21 C16 C17 C18 -0.2(4)
C15 C16 C17 C18 179.9(3)
C16 C17 C18 C19 -0.9(4)
C17 C18 C19 C20 1.3(5)
C18 C19 C20 C21 -0.6(5)
C17 C16 C21 C20 0.9(4)
C15 C16 C21 C20 -179.2(3)
C19 C20 C21 C16 -0.6(5)
