#------------------------------------------------------------------------------
#$Date: 2023-12-22 16:07:40 +0100 (Fri 22 de Dec de 2023) $
#$Revision: 288505 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154037.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_7154037
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         'C16 H13 N O4'
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 114.805(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.374(8)
_cell_length_b                   5.4040(12)
_cell_length_c                   16.122(4)
_cell_measurement_reflns_used    825
_cell_measurement_temperature    261(2)
_cell_measurement_theta_max      20.80
_cell_measurement_theta_min      2.77
_cell_volume                     2560.3(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      261(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.6463
_diffrn_reflns_av_sigmaI/netI    0.3255
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21895
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.2715
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0177P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1825
_reflns_number_gt                1072
_reflns_number_total             2953
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01693a5.cif
_cod_data_source_block           R6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        2560.3(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7154037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.17645(11) 0.6300(6) 0.1380(2) 0.0214(9) Uani 1 1 d .
H1 H 0.2005 0.5918 0.1857 0.026 Uiso 1 1 calc R
O1 O 0.02834(12) 0.8941(8) -0.1279(3) 0.0680(13) Uani 1 1 d .
O2 O 0.01485(9) 1.2424(6) -0.0722(2) 0.0385(10) Uani 1 1 d .
O3 O 0.24359(9) 0.2601(5) 0.1762(2) 0.0252(8) Uani 1 1 d .
O4 O 0.23624(9) 0.0003(6) 0.0620(2) 0.0277(8) Uani 1 1 d .
C1 C 0.16184(13) 0.5142(9) 0.0553(3) 0.0202(11) Uani 1 1 d .
C2 C 0.12159(12) 0.6300(8) -0.0073(3) 0.0204(11) Uani 1 1 d .
C3 C 0.10091(13) 0.5380(9) -0.0966(3) 0.0232(11) Uani 1 1 d .
H3 H 0.0746 0.6114 -0.1394 0.028 Uiso 1 1 calc R
C4 C 0.12001(14) 0.3367(9) -0.1205(3) 0.0261(12) Uani 1 1 d .
H4 H 0.1060 0.2743 -0.1796 0.031 Uiso 1 1 calc R
C5 C 0.15923(13) 0.2263(8) -0.0588(3) 0.0244(12) Uani 1 1 d .
H5 H 0.1710 0.0907 -0.0772 0.029 Uiso 1 1 calc R
C6 C 0.18179(13) 0.3135(9) 0.0310(3) 0.0217(11) Uani 1 1 d .
C7 C 0.14644(13) 0.8186(8) 0.1331(3) 0.0203(11) Uani 1 1 d .
C8 C 0.11105(13) 0.8261(8) 0.0432(3) 0.0196(11) Uani 1 1 d .
C9 C 0.07759(13) 1.0103(9) 0.0251(3) 0.0224(11) Uani 1 1 d .
C10 C 0.08063(14) 1.1723(9) 0.0941(3) 0.0257(12) Uani 1 1 d .
H10 H 0.0588 1.2956 0.0818 0.031 Uiso 1 1 calc R
C11 C 0.11592(14) 1.1542(9) 0.1822(3) 0.0290(12) Uani 1 1 d .
H11 H 0.1169 1.2641 0.2274 0.035 Uiso 1 1 calc R
C12 C 0.14902(13) 0.9768(8) 0.2027(3) 0.0249(12) Uani 1 1 d .
H12 H 0.1723 0.9632 0.2611 0.030 Uiso 1 1 calc R
C13 C 0.03884(14) 1.0370(9) -0.0659(3) 0.0251(12) Uani 1 1 d .
C14 C -0.02289(14) 1.2932(9) -0.1576(3) 0.0359(14) Uani 1 1 d .
H14A H -0.0245 1.1686 -0.2013 0.054 Uiso 1 1 calc R
H14B H -0.0189 1.4526 -0.1796 0.054 Uiso 1 1 calc R
H14C H -0.0506 1.2925 -0.1493 0.054 Uiso 1 1 calc R
C15 C 0.22314(14) 0.1929(9) 0.0972(3) 0.0223(11) Uani 1 1 d .
C16 C 0.27506(14) -0.1357(9) 0.1251(3) 0.0334(13) Uani 1 1 d .
H16A H 0.3013 -0.0298 0.1476 0.050 Uiso 1 1 calc R
H16B H 0.2807 -0.2751 0.0944 0.050 Uiso 1 1 calc R
H16C H 0.2690 -0.1928 0.1754 0.050 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
C1 N1 C7 109.5(4)
C1 N1 H1 125.2
C7 N1 H1 125.2
C13 O2 C14 117.9(4)
C15 O4 C16 115.8(3)
N1 C1 C6 128.1(4)
N1 C1 C2 109.4(4)
C6 C1 C2 122.5(4)
C3 C2 C1 118.5(4)
C3 C2 C8 135.1(4)
C1 C2 C8 106.4(4)
C4 C3 C2 119.2(4)
C4 C3 H3 120.4
C2 C3 H3 120.4
C5 C4 C3 121.6(4)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 121.6(4)
C4 C5 H5 119.2
C6 C5 H5 119.2
C1 C6 C5 116.6(4)
C1 C6 C15 121.8(4)
C5 C6 C15 121.5(4)
C12 C7 N1 127.2(4)
C12 C7 C8 123.9(4)
N1 C7 C8 108.9(4)
C9 C8 C7 116.8(4)
C9 C8 C2 137.4(4)
C7 C8 C2 105.7(4)
C10 C9 C8 119.4(4)
C10 C9 C13 118.5(4)
C8 C9 C13 122.1(4)
C9 C10 C11 121.5(4)
C9 C10 H10 119.3
C11 C10 H10 119.3
C12 C11 C10 121.0(4)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C7 117.5(4)
C11 C12 H12 121.3
C7 C12 H12 121.3
O1 C13 O2 121.4(4)
O1 C13 C9 126.2(4)
O2 C13 C9 112.4(4)
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 O4 123.1(4)
O3 C15 C6 123.9(4)
O4 C15 C6 113.1(4)
O4 C16 H16A 109.5
O4 C16 H16B 109.5
H16A C16 H16B 109.5
O4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.365(5)
N1 C7 1.388(5)
N1 H1 0.8600
O1 C13 1.195(5)
O2 C13 1.334(5)
O2 C14 1.433(5)
O3 C15 1.218(5)
O4 C15 1.337(5)
O4 C16 1.443(5)
C1 C6 1.400(6)
C1 C2 1.416(5)
C2 C3 1.399(6)
C2 C8 1.461(6)
C3 C4 1.383(6)
C3 H3 0.9300
C4 C5 1.377(6)
C4 H4 0.9300
C5 C6 1.401(6)
C5 H5 0.9300
C6 C15 1.469(6)
C7 C12 1.385(5)
C7 C8 1.422(6)
C8 C9 1.409(6)
C9 C10 1.387(6)
C9 C13 1.483(6)
C10 C11 1.404(6)
C10 H10 0.9300
C11 C12 1.371(6)
C11 H11 0.9300
C12 H12 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
C7 N1 C1 C6 -179.2(4)
C7 N1 C1 C2 1.1(4)
N1 C1 C2 C3 -179.8(3)
C6 C1 C2 C3 0.6(6)
N1 C1 C2 C8 -1.4(4)
C6 C1 C2 C8 179.0(4)
C1 C2 C3 C4 0.7(6)
C8 C2 C3 C4 -177.1(4)
C2 C3 C4 C5 -0.8(6)
C3 C4 C5 C6 -0.3(7)
N1 C1 C6 C5 178.8(4)
C2 C1 C6 C5 -1.7(6)
N1 C1 C6 C15 1.5(6)
C2 C1 C6 C15 -178.9(4)
C4 C5 C6 C1 1.5(6)
C4 C5 C6 C15 178.8(4)
C1 N1 C7 C12 179.2(4)
C1 N1 C7 C8 -0.4(4)
C12 C7 C8 C9 1.4(6)
N1 C7 C8 C9 -179.0(3)
C12 C7 C8 C2 179.9(4)
N1 C7 C8 C2 -0.5(4)
C3 C2 C8 C9 -2.8(9)
C1 C2 C8 C9 179.2(5)
C3 C2 C8 C7 179.1(4)
C1 C2 C8 C7 1.1(4)
C7 C8 C9 C10 0.1(6)
C2 C8 C9 C10 -177.8(4)
C7 C8 C9 C13 -179.8(4)
C2 C8 C9 C13 2.3(8)
C8 C9 C10 C11 -1.1(6)
C13 C9 C10 C11 178.7(4)
C9 C10 C11 C12 0.8(7)
C10 C11 C12 C7 0.5(6)
N1 C7 C12 C11 178.8(4)
C8 C7 C12 C11 -1.7(6)
C14 O2 C13 O1 -2.9(7)
C14 O2 C13 C9 178.4(4)
C10 C9 C13 O1 -169.7(5)
C8 C9 C13 O1 10.2(7)
C10 C9 C13 O2 8.9(6)
C8 C9 C13 O2 -171.2(4)
C16 O4 C15 O3 3.6(6)
C16 O4 C15 C6 -176.4(3)
C1 C6 C15 O3 -1.9(6)
C5 C6 C15 O3 -179.1(4)
C1 C6 C15 O4 178.1(4)
C5 C6 C15 O4 0.9(6)
