#------------------------------------------------------------------------------
#$Date: 2025-02-01 09:07:15 +0200 (Sat, 01 Feb 2025) $
#$Revision: 297561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159732.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_7159732
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_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.41
_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_method           SHELXL-2019/1
_audit_update_record
;
2023-06-06 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.924(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1412(11)
_cell_length_b                   12.7990(9)
_cell_length_c                   12.1671(7)
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      25.351
_cell_measurement_theta_min      1.865
_cell_volume                     1700.5(2)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      149(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  Bruker_D8_venture
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6831
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.551
_diffrn_reflns_theta_min         1.865
_diffrn_source                   Mo
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0451
_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)+(0.0483P)²+0.6936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2667
_reflns_number_total             3166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01827j2.cif
_cod_data_source_block           mo_CARB2OMe_0m_a
_cod_depositor_comments
;
Adding full bibliography for 7159731--7159734.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.71 H2 N0.35 O0.12'
_cod_original_formula_weight         41.34
_cod_original_formula_units_Z            34
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159732
_shelx_shelxl_version_number     2019/1
_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.
;
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
O001 O 0.80045(13) 0.67915(9) 0.82148(11) 0.0313(3) Uani 1 1 d . . . . .
N002 N 0.68746(14) 0.47486(10) 0.45006(12) 0.0233(3) Uani 1 1 d . . . . .
N003 N 0.76231(14) 0.33848(10) 0.59103(12) 0.0245(3) Uani 1 1 d . . . . .
N004 N 0.80615(15) 0.34681(11) 0.41832(13) 0.0280(3) Uani 1 1 d . . . . .
C005 C 0.67515(16) 0.55051(11) 0.52809(15) 0.0214(3) Uani 1 1 d . . . . .
C006 C 0.91978(17) 0.47797(12) 0.82448(15) 0.0233(4) Uani 1 1 d . . . . .
H006 H 0.866852 0.475179 0.863292 0.028 Uiso 1 1 calc R U . . .
C007 C 0.88054(16) 0.52742(11) 0.71166(14) 0.0214(3) Uani 1 1 d . . . . .
C008 C 0.75604(16) 0.38182(12) 0.48929(14) 0.0218(3) Uani 1 1 d . . . . .
C009 C 0.75741(16) 0.57557(12) 0.64835(15) 0.0220(3) Uani 1 1 d . . . . .
C00A C 0.56746(17) 0.60770(12) 0.46147(15) 0.0232(4) Uani 1 1 d . . . . .
C00B C 0.72003(17) 0.65636(12) 0.70298(15) 0.0245(4) Uani 1 1 d . . . . .
C00C C 0.96154(17) 0.53138(12) 0.65798(15) 0.0238(4) Uani 1 1 d . . . . .
H00C H 0.937697 0.566393 0.582145 0.029 Uiso 1 1 calc R U . . .
C00D C 0.51339(17) 0.56796(12) 0.33741(15) 0.0242(4) Uani 1 1 d . . . . .
C00E C 1.03481(17) 0.43283(12) 0.88090(15) 0.0267(4) Uani 1 1 d . . . . .
H00E H 1.059769 0.399786 0.958023 0.032 Uiso 1 1 calc R U . . .
C00F C 0.61094(18) 0.71199(13) 0.63899(16) 0.0276(4) Uani 1 1 d . . . . .
H00F H 0.588262 0.765656 0.679054 0.033 Uiso 1 1 calc R U . . .
C00G C 0.59005(17) 0.48741(12) 0.33263(15) 0.0241(4) Uani 1 1 d . . . . .
C00H C 0.87502(19) 0.26184(13) 0.45948(16) 0.0309(4) Uani 1 1 d . . . . .
H00H H 0.913345 0.233860 0.412587 0.037 Uiso 1 1 calc R U . . .
C00I C 1.07640(18) 0.48484(13) 0.71397(16) 0.0287(4) Uani 1 1 d . . . . .
H00I H 1.129518 0.486910 0.675340 0.034 Uiso 1 1 calc R U . . .
C00J C 0.83284(19) 0.25342(12) 0.62897(15) 0.0286(4) Uani 1 1 d . . . . .
H00J H 0.841126 0.220196 0.702001 0.034 Uiso 1 1 calc R U . . .
C00K C 0.53648(17) 0.68920(12) 0.51834(16) 0.0264(4) Uani 1 1 d . . . . .
H00K H 0.464362 0.728924 0.474176 0.032 Uiso 1 1 calc R U . . .
C00L C 1.11394(18) 0.43513(13) 0.82665(16) 0.0290(4) Uani 1 1 d . . . . .
H00L H 1.192439 0.403412 0.865438 0.035 Uiso 1 1 calc R U . . .
C00M C 0.40940(18) 0.59539(13) 0.23206(16) 0.0291(4) Uani 1 1 d . . . . .
H00M H 0.357244 0.649921 0.234106 0.035 Uiso 1 1 calc R U . . .
C00N C 0.89372(19) 0.21202(13) 0.56729(16) 0.0325(4) Uani 1 1 d . . . . .
H00N H 0.945579 0.152766 0.596642 0.039 Uiso 1 1 calc R U . . .
C00O C 0.56419(18) 0.43297(14) 0.22519(15) 0.0296(4) Uani 1 1 d . . . . .
H00O H 0.615852 0.378238 0.222591 0.036 Uiso 1 1 calc R U . . .
C00P C 0.7640(2) 0.75672(14) 0.88303(18) 0.0347(4) Uani 1 1 d . . . . .
H00A H 0.826211 0.762634 0.967867 0.052 Uiso 1 1 calc R U . . .
H00B H 0.685497 0.736737 0.881784 0.052 Uiso 1 1 calc R U . . .
H00D H 0.755070 0.824100 0.841737 0.052 Uiso 1 1 calc R U . . .
C00Q C 0.38336(19) 0.54234(15) 0.12500(16) 0.0329(4) Uani 1 1 d . . . . .
H00Q H 0.312893 0.560582 0.052687 0.039 Uiso 1 1 calc R U . . .
C00R C 0.4600(2) 0.46174(15) 0.12194(17) 0.0339(4) Uani 1 1 d . . . . .
H00R H 0.440057 0.425847 0.047293 0.041 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
C00B O001 C00P 117.24(15) . . ?
C005 N002 C00G 108.38(13) . . ?
C005 N002 C008 124.94(14) . . ?
C00G N002 C008 123.25(13) . . ?
C008 N003 C00J 115.42(15) . . ?
C00H N004 C008 114.91(14) . . ?
C009 C005 C00A 122.80(14) . . ?
C009 C005 N002 128.58(15) . . ?
C00A C005 N002 108.38(14) . . ?
C00E C006 C007 120.96(16) . . ?
C006 C007 C00C 117.97(16) . . ?
C006 C007 C009 122.23(15) . . ?
C00C C007 C009 119.79(14) . . ?
N003 C008 N004 127.38(15) . . ?
N003 C008 N002 116.92(14) . . ?
N004 C008 N002 115.70(14) . . ?
C005 C009 C00B 115.56(15) . . ?
C005 C009 C007 122.93(14) . . ?
C00B C009 C007 121.31(15) . . ?
C00K C00A C005 119.28(15) . . ?
C00K C00A C00D 133.08(16) . . ?
C005 C00A C00D 107.54(14) . . ?
O001 C00B C00F 122.72(15) . . ?
O001 C00B C009 115.08(15) . . ?
C00F C00B C009 122.16(15) . . ?
C00I C00C C007 120.99(15) . . ?
C00M C00D C00G 119.73(16) . . ?
C00M C00D C00A 133.19(16) . . ?
C00G C00D C00A 107.07(15) . . ?
C00L C00E C006 120.99(15) . . ?
C00K C00F C00B 120.32(15) . . ?
C00O C00G C00D 121.63(17) . . ?
C00O C00G N002 129.79(16) . . ?
C00D C00G N002 108.57(14) . . ?
N004 C00H C00N 123.31(16) . . ?
C00C C00I C00L 120.25(16) . . ?
N003 C00J C00N 122.95(15) . . ?
C00F C00K C00A 119.65(16) . . ?
C00E C00L C00I 118.81(17) . . ?
C00Q C00M C00D 119.09(17) . . ?
C00J C00N C00H 115.88(16) . . ?
C00R C00O C00G 117.38(17) . . ?
C00M C00Q C00R 120.51(18) . . ?
C00O C00R C00Q 121.66(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
O001 C00B 1.373(2) . ?
O001 C00P 1.426(2) . ?
N002 C005 1.409(2) . ?
N002 C00G 1.410(2) . ?
N002 C008 1.411(2) . ?
N003 C008 1.328(2) . ?
N003 C00J 1.336(2) . ?
N004 C00H 1.329(2) . ?
N004 C008 1.333(2) . ?
C005 C009 1.401(2) . ?
C005 C00A 1.406(2) . ?
C006 C00E 1.385(3) . ?
C006 C007 1.393(2) . ?
C007 C00C 1.399(2) . ?
C007 C009 1.484(2) . ?
C009 C00B 1.407(2) . ?
C00A C00K 1.391(2) . ?
C00A C00D 1.450(2) . ?
C00B C00F 1.402(3) . ?
C00C C00I 1.390(3) . ?
C00D C00M 1.395(2) . ?
C00D C00G 1.407(2) . ?
C00E C00L 1.384(3) . ?
C00F C00K 1.377(2) . ?
C00G C00O 1.391(2) . ?
C00H C00N 1.385(3) . ?
C00I C00L 1.395(2) . ?
C00J C00N 1.369(3) . ?
C00M C00Q 1.378(3) . ?
C00O C00R 1.387(3) . ?
C00Q C00R 1.400(3) . ?
