#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:36:42 +0200 (mar 06 de oct de 2020) $
#$Revision: 257643 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/97/7059720.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_7059720
loop_
_publ_author_name
'Singh, Manpreet'
'Paul, Avijit Kumar'
'Singh, Virender'
_publ_section_title
;
 A transition metal-free approach towards the regioselective synthesis of
 β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12370
_journal_page_last               12383
_journal_paper_doi               10.1039/D0NJ02315A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C28 H25 N3 O5'
_chemical_formula_weight         483.51
_chemical_name_common            'Pyrrole derivative'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-04-14 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.537(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9292(12)
_cell_length_b                   10.5655(10)
_cell_length_c                   17.6719(16)
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.01
_cell_volume                     2411.7(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_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  0.0739
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23039
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Block like'
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0608
_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)+(0.0921P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                2241
_reflns_number_total             4205
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0nj02315a2.cif
_cod_data_source_block           Compound(1)
_cod_depositor_comments
;Adding full bibliography for 7059720.cif.

 Adding full bibliography for 7059720.cif.
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7059720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67113(15) 0.2926(2) 0.29727(12) 0.0764(7) Uani 1 1 d . . .
O3 O 0.78096(16) 0.89180(19) 0.42567(13) 0.0801(7) Uani 1 1 d . . .
N1 N 0.76440(16) 0.5182(2) 0.43245(12) 0.0510(6) Uani 1 1 d . . .
N2 N 0.57788(17) 0.7449(2) 0.50998(13) 0.0578(6) Uani 1 1 d . . .
O2 O 0.82982(17) 0.3244(2) 0.34509(13) 0.0934(8) Uani 1 1 d . . .
N3 N 0.99307(17) 0.6183(2) 0.55478(13) 0.0618(7) Uani 1 1 d . . .
H3 H 1.0476 0.5863 0.5769 0.074 Uiso 1 1 calc R . .
O4 O 0.79297(19) 0.6232(3) 0.68009(12) 0.0961(8) Uani 1 1 d . . .
C23 C 0.9501(2) 0.9102(3) 0.38220(15) 0.0533(7) Uani 1 1 d . . .
C5 C 0.55788(19) 0.5872(2) 0.42311(15) 0.0492(7) Uani 1 1 d . . .
C6 C 0.4591(2) 0.6468(3) 0.43132(16) 0.0529(7) Uani 1 1 d . . .
C3 C 0.6953(2) 0.4573(2) 0.38590(15) 0.0492(7) Uani 1 1 d . . .
O5 O 0.94308(19) 0.5239(3) 0.69183(13) 0.1230(11) Uani 1 1 d . . .
C21 C 0.8979(2) 0.7456(3) 0.47701(15) 0.0516(7) Uani 1 1 d . . .
C14 C 0.73373(19) 0.6134(2) 0.47530(15) 0.0481(7) Uani 1 1 d . . .
C13 C 0.6293(2) 0.6504(2) 0.47243(15) 0.0492(7) Uani 1 1 d . . .
C4 C 0.5921(2) 0.4889(2) 0.37899(15) 0.0538(7) Uani 1 1 d . . .
H4 H 0.5469 0.4457 0.3458 0.065 Uiso 1 1 calc R . .
C11 C 0.4740(2) 0.7435(3) 0.48456(16) 0.0571(8) Uani 1 1 d . . .
C15 C 0.81943(19) 0.6759(3) 0.52302(14) 0.0506(7) Uani 1 1 d . . .
H15 H 0.7886 0.7358 0.5578 0.061 Uiso 1 1 calc R . .
C2 C 0.7400(2) 0.3528(3) 0.34200(17) 0.0597(8) Uani 1 1 d . . .
C22 C 0.8701(2) 0.8499(3) 0.42859(16) 0.0567(8) Uani 1 1 d . . .
C20 C 0.9938(2) 0.7085(3) 0.50271(15) 0.0535(7) Uani 1 1 d . . .
H20 H 1.0544 0.7433 0.4853 0.064 Uiso 1 1 calc R . .
C17 C 0.8674(2) 0.5808(3) 0.65306(17) 0.0662(9) Uani 1 1 d . . .
C25 C 1.0263(2) 0.8435(3) 0.34720(16) 0.0666(9) Uani 1 1 d . . .
H25 H 1.0283 0.7557 0.3510 0.080 Uiso 1 1 calc R . .
C16 C 0.8876(2) 0.5810(3) 0.56953(15) 0.0570(8) Uani 1 1 d . . .
H16 H 0.8753 0.4957 0.5493 0.068 Uiso 1 1 calc R . .
C7 C 0.3608(2) 0.6266(3) 0.39715(18) 0.0655(8) Uani 1 1 d . . .
H7 H 0.3492 0.5615 0.3624 0.079 Uiso 1 1 calc R . .
C10 C 0.3934(2) 0.8230(3) 0.50409(18) 0.0703(9) Uani 1 1 d . . .
H10 H 0.4037 0.8873 0.5396 0.084 Uiso 1 1 calc R . .
C24 C 0.9464(2) 1.0398(3) 0.37278(17) 0.0714(9) Uani 1 1 d . . .
H24 H 0.8937 1.0857 0.3942 0.086 Uiso 1 1 calc R . .
C8 C 0.2818(2) 0.7063(3) 0.4165(2) 0.0766(10) Uani 1 1 d . . .
H8 H 0.2161 0.6953 0.3940 0.092 Uiso 1 1 calc R . .
C9 C 0.2986(2) 0.8026(3) 0.4689(2) 0.0785(10) Uani 1 1 d . . .
H9 H 0.2437 0.8548 0.4805 0.094 Uiso 1 1 calc R . .
C27 C 1.0997(3) 0.9057(4) 0.30652(19) 0.0833(10) Uani 1 1 d . . .
H27 H 1.1509 0.8604 0.2829 0.100 Uiso 1 1 calc R . .
C28 C 1.0960(3) 1.0357(4) 0.3014(2) 0.0891(11) Uani 1 1 d . . .
H28 H 1.1471 1.0787 0.2763 0.107 Uiso 1 1 calc R . .
C1 C 0.7112(3) 0.1935(3) 0.2500(2) 0.0922(12) Uani 1 1 d . . .
H1A H 0.7688 0.2256 0.2232 0.138 Uiso 1 1 calc R . .
H1B H 0.6579 0.1660 0.2142 0.138 Uiso 1 1 calc R . .
H1C H 0.7337 0.1234 0.2811 0.138 Uiso 1 1 calc R . .
C26 C 1.0184(3) 1.1020(3) 0.3326(2) 0.0880(11) Uani 1 1 d . . .
H26 H 1.0145 1.1893 0.3266 0.106 Uiso 1 1 calc R . .
C12 C 0.6187(3) 0.8338(3) 0.5665(2) 0.0979(13) Uani 1 1 d . . .
H12A H 0.6415 0.7886 0.6113 0.147 Uiso 1 1 calc R . .
H12B H 0.5655 0.8928 0.5788 0.147 Uiso 1 1 calc R . .
H12C H 0.6760 0.8789 0.5467 0.147 Uiso 1 1 calc R . .
C19 C 1.0209(5) 0.5812(4) 0.8099(2) 0.142(2) Uani 1 1 d . . .
H19A H 1.0814 0.5306 0.8027 0.213 Uiso 1 1 calc R . .
H19B H 1.0097 0.5886 0.8631 0.213 Uiso 1 1 calc R . .
H19C H 1.0306 0.6638 0.7888 0.213 Uiso 1 1 calc R . .
C18 C 0.9381(4) 0.5256(8) 0.7749(2) 0.200(3) Uani 1 1 d . . .
H18A H 0.8760 0.5703 0.7884 0.240 Uiso 1 1 calc R . .
H18B H 0.9327 0.4393 0.7930 0.240 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 116.2(2) . . ?
C14 N1 C3 120.1(2) . . ?
C13 N2 C11 108.3(2) . . ?
C13 N2 C12 128.9(2) . . ?
C11 N2 C12 122.8(2) . . ?
C20 N3 C16 110.8(2) . . ?
C20 N3 H3 124.6 . . ?
C16 N3 H3 124.6 . . ?
C25 C23 C24 118.3(3) . . ?
C25 C23 C22 123.7(3) . . ?
C24 C23 C22 118.0(3) . . ?
C4 C5 C13 119.1(2) . . ?
C4 C5 C6 133.9(3) . . ?
C13 C5 C6 106.9(2) . . ?
C11 C6 C7 119.9(3) . . ?
C11 C6 C5 106.9(2) . . ?
C7 C6 C5 133.2(3) . . ?
N1 C3 C4 123.5(2) . . ?
N1 C3 C2 114.3(2) . . ?
C4 C3 C2 122.3(3) . . ?
C17 O5 C18 116.7(3) . . ?
C20 C21 C22 128.5(3) . . ?
C20 C21 C15 107.6(2) . . ?
C22 C21 C15 122.5(2) . . ?
N1 C14 C13 120.0(2) . . ?
N1 C14 C15 114.7(2) . . ?
C13 C14 C15 125.3(2) . . ?
N2 C13 C14 131.7(3) . . ?
N2 C13 C5 108.8(2) . . ?
C14 C13 C5 119.5(2) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C10 C11 C6 121.7(3) . . ?
C10 C11 N2 129.2(3) . . ?
C6 C11 N2 109.1(2) . . ?
C14 C15 C21 113.8(2) . . ?
C14 C15 C16 113.5(2) . . ?
C21 C15 C16 102.7(2) . . ?
C14 C15 H15 108.9 . . ?
C21 C15 H15 108.9 . . ?
C16 C15 H15 108.9 . . ?
O2 C2 O1 122.0(3) . . ?
O2 C2 C3 124.2(3) . . ?
O1 C2 C3 113.7(2) . . ?
O3 C22 C21 120.7(3) . . ?
O3 C22 C23 119.6(3) . . ?
C21 C22 C23 119.7(2) . . ?
N3 C20 C21 113.9(3) . . ?
N3 C20 H20 123.1 . . ?
C21 C20 H20 123.1 . . ?
O4 C17 O5 124.3(3) . . ?
O4 C17 C16 125.0(3) . . ?
O5 C17 C16 110.7(3) . . ?
C23 C25 C27 120.7(3) . . ?
C23 C25 H25 119.6 . . ?
C27 C25 H25 119.6 . . ?
N3 C16 C17 112.3(2) . . ?
N3 C16 C15 104.2(2) . . ?
C17 C16 C15 113.6(2) . . ?
N3 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C15 C16 H16 108.8 . . ?
C8 C7 C6 118.0(3) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C9 C10 C11 117.2(3) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 H10 121.4 . . ?
C26 C24 C23 121.3(3) . . ?
C26 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C28 C27 C25 119.1(3) . . ?
C28 C27 H27 120.5 . . ?
C25 C27 H27 120.5 . . ?
C26 C28 C27 120.7(3) . . ?
C26 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 C26 C24 119.7(3) . . ?
C28 C26 H26 120.1 . . ?
C24 C26 H26 120.1 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C19 C18 O5 113.2(4) . . ?
C19 C18 H18A 108.9 . . ?
O5 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
O5 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
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
O1 C2 1.327(3) . ?
O1 C1 1.450(3) . ?
O3 C22 1.233(3) . ?
N1 C14 1.331(3) . ?
N1 C3 1.350(3) . ?
N2 C13 1.385(3) . ?
N2 C11 1.398(3) . ?
N2 C12 1.453(4) . ?
O2 C2 1.198(3) . ?
N3 C20 1.325(3) . ?
N3 C16 1.454(3) . ?
N3 H3 0.8600 . ?
O4 C17 1.181(3) . ?
C23 C25 1.380(4) . ?
C23 C24 1.380(4) . ?
C23 C22 1.491(4) . ?
C5 C4 1.383(4) . ?
C5 C13 1.410(4) . ?
C5 C6 1.438(4) . ?
C6 C11 1.396(4) . ?
C6 C7 1.398(4) . ?
C3 C4 1.376(3) . ?
C3 C2 1.481(4) . ?
O5 C17 1.315(4) . ?
O5 C18 1.473(5) . ?
C21 C20 1.359(4) . ?
C21 C22 1.432(4) . ?
C21 C15 1.518(3) . ?
C14 C13 1.404(3) . ?
C14 C15 1.514(3) . ?
C4 H4 0.9300 . ?
C11 C10 1.394(4) . ?
C15 C16 1.547(4) . ?
C15 H15 0.9800 . ?
C20 H20 0.9300 . ?
C17 C16 1.510(4) . ?
C25 C27 1.382(4) . ?
C25 H25 0.9300 . ?
C16 H16 0.9800 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C10 C9 1.366(4) . ?
C10 H10 0.9300 . ?
C24 C26 1.365(4) . ?
C24 H24 0.9300 . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C27 C28 1.377(5) . ?
C27 H27 0.9300 . ?
C28 C26 1.360(5) . ?
C28 H28 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C26 H26 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C19 C18 1.347(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
