#------------------------------------------------------------------------------
#$Date: 2020-05-01 23:33:23 +0300 (Fri, 01 May 2020) $
#$Revision: 251381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038319.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_4038319
loop_
_publ_author_name
'Vannada, Jagadeshwar'
'Sulthan, Mahesh'
'Arun, Doma'
'Dada, Ravikrishna'
'Yaragorla, Srinivasarao'
_publ_section_title
;
 Regiodivergent Synthesis of Penta-Substituted Pyrroles through a Cascade
 [3+2] Cyclisation of C-acylimines with Activated-Alkynes and Aromatic
 Nucleophiles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00712
_journal_year                    2020
_chemical_formula_sum            'C29 H24 N2 O4'
_chemical_formula_weight         464.50
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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                 103.496(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.002(3)
_cell_length_b                   11.4379(17)
_cell_length_c                   18.394(3)
_cell_measurement_reflns_used    9164
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.86
_cell_volume                     4910.3(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            54926
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0501
_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)+(0.0601P)²+3.7003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                3957
_reflns_number_total             5020
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo0c00712_si_002.cif
_cod_data_source_block           ysr44b_0m_a_a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4038319
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36301(6) 0.77380(12) 0.48405(7) 0.0602(4) Uani 1 1 d . . .
O2 O 0.35357(6) 1.00267(12) 0.40171(8) 0.0618(4) Uani 1 1 d . . .
N1 N 0.37452(6) 0.66285(11) 0.30516(7) 0.0396(3) Uani 1 1 d . . .
O3 O 0.39491(7) 0.59630(12) 0.46318(8) 0.0642(4) Uani 1 1 d . . .
O4 O 0.26523(6) 0.92818(13) 0.37942(9) 0.0674(4) Uani 1 1 d . . .
N2 N 0.38741(8) 0.58205(15) 0.07295(9) 0.0553(4) Uani 1 1 d . . .
C1 C 0.36186(7) 0.72866(14) 0.36235(9) 0.0390(4) Uani 1 1 d . . .
C2 C 0.33671(7) 0.83117(14) 0.33157(9) 0.0381(4) Uani 1 1 d . . .
C3 C 0.33352(7) 0.82834(14) 0.25392(9) 0.0385(4) Uani 1 1 d . . .
C4 C 0.35814(7) 0.72325(14) 0.23931(9) 0.0384(4) Uani 1 1 d . . .
C5 C 0.37447(7) 0.68472(14) 0.17085(9) 0.0393(4) Uani 1 1 d . . .
C6 C 0.31358(8) 0.92415(15) 0.37323(9) 0.0430(4) Uani 1 1 d . . .
C7 C 0.37524(8) 0.68966(16) 0.43986(9) 0.0446(4) Uani 1 1 d . . .
C8 C 0.39621(7) 0.54436(14) 0.31093(9) 0.0405(4) Uani 1 1 d . . .
C9 C 0.41420(7) 0.74662(15) 0.13735(9) 0.0425(4) Uani 1 1 d . . .
C10 C 0.30647(7) 0.91638(16) 0.19770(9) 0.0457(4) Uani 1 1 d . . .
C11 C 0.42140(8) 0.67908(16) 0.07612(9) 0.0469(4) Uani 1 1 d . . .
C12 C 0.35990(8) 0.58558(16) 0.13015(10) 0.0504(4) Uani 1 1 d . . .
H12 H 0.3349 0.5286 0.1398 0.060 Uiso 1 1 calc R . .
C13 C 0.45339(8) 0.52328(17) 0.32182(11) 0.0530(5) Uani 1 1 d . . .
H13 H 0.4792 0.5849 0.3259 0.064 Uiso 1 1 calc R . .
C14 C 0.35763(9) 0.45383(16) 0.30391(13) 0.0580(5) Uani 1 1 d . . .
H14 H 0.3186 0.4689 0.2958 0.070 Uiso 1 1 calc R . .
C15 C 0.27604(9) 0.8818(2) 0.12728(11) 0.0638(6) Uani 1 1 d . . .
H15 H 0.2727 0.8027 0.1153 0.077 Uiso 1 1 calc R . .
C16 C 0.30916(9) 1.03532(17) 0.21394(12) 0.0586(5) Uani 1 1 d . . .
H16 H 0.3290 1.0604 0.2610 0.070 Uiso 1 1 calc R . .
C17 C 0.47259(9) 0.40809(19) 0.32670(13) 0.0634(5) Uani 1 1 d . . .
H17 H 0.5116 0.3933 0.3343 0.076 Uiso 1 1 calc R . .
C18 C 0.43506(10) 0.31527(17) 0.32055(12) 0.0605(5) Uani 1 1 d . . .
C19 C 0.37762(10) 0.34035(18) 0.30903(14) 0.0671(6) Uani 1 1 d . . .
H19 H 0.3515 0.2791 0.3046 0.081 Uiso 1 1 calc R . .
C20 C 0.44571(10) 0.84958(19) 0.15433(13) 0.0660(6) Uani 1 1 d . . .
H20 H 0.4417 0.8963 0.1942 0.079 Uiso 1 1 calc R . .
C00R C 0.45933(10) 0.7112(2) 0.03263(12) 0.0663(6) Uani 1 1 d . . .
H00R H 0.4639 0.6655 -0.0073 0.080 Uiso 1 1 calc R . .
C00S C 0.25460(11) 1.0821(3) 0.09236(17) 0.0897(9) Uani 1 1 d . . .
H00S H 0.2380 1.1375 0.0569 0.108 Uiso 1 1 calc R . .
C00T C 0.37560(13) 0.7496(3) 0.56281(12) 0.0893(9) Uani 1 1 d . . .
H00A H 0.3651 0.8158 0.5888 0.134 Uiso 1 1 calc R . .
H00B H 0.4158 0.7346 0.5804 0.134 Uiso 1 1 calc R . .
H00C H 0.3543 0.6823 0.5718 0.134 Uiso 1 1 calc R . .
C00U C 0.48941(12) 0.8124(3) 0.05096(16) 0.0840(8) Uani 1 1 d . . .
H00U H 0.5148 0.8362 0.0227 0.101 Uiso 1 1 calc R . .
C00V C 0.28296(11) 1.1169(2) 0.16164(17) 0.0796(7) Uani 1 1 d . . .
H00V H 0.2848 1.1959 0.1740 0.095 Uiso 1 1 calc R . .
C00W C 0.25035(11) 0.9648(3) 0.07438(13) 0.0886(9) Uani 1 1 d . . .
H00W H 0.2304 0.9411 0.0271 0.106 Uiso 1 1 calc R . .
C00X C 0.48298(12) 0.8807(3) 0.11081(17) 0.0879(8) Uani 1 1 d . . .
H00X H 0.5043 0.9490 0.1218 0.105 Uiso 1 1 calc R . .
C00Y C 0.45596(13) 0.1899(2) 0.32629(18) 0.0911(9) Uani 1 1 d . . .
H00D H 0.4238 0.1379 0.3208 0.137 Uiso 1 1 calc R . .
H00E H 0.4816 0.1776 0.3742 0.137 Uiso 1 1 calc R . .
H00F H 0.4757 0.1746 0.2875 0.137 Uiso 1 1 calc R . .
C00Z C 0.33653(15) 1.0947(2) 0.44612(18) 0.0989(10) Uani 1 1 d . . .
H00G H 0.3683 1.1465 0.4637 0.148 Uiso 1 1 calc R . .
H00H H 0.3249 1.0609 0.4880 0.148 Uiso 1 1 calc R . .
H00I H 0.3051 1.1376 0.4160 0.148 Uiso 1 1 calc R . .
H1 H 0.3854(10) 0.524(2) 0.0413(14) 0.073(7) Uiso 1 1 d . . .
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
C7 O1 C00T 116.79(16) . . ?
C6 O2 C00Z 116.12(18) . . ?
C4 N1 C1 109.23(13) . . ?
C4 N1 C8 124.15(13) . . ?
C1 N1 C8 126.36(13) . . ?
C12 N2 C11 109.45(15) . . ?
C12 N2 H1 125.0(16) . . ?
C11 N2 H1 125.5(16) . . ?
C2 C1 N1 107.65(13) . . ?
C2 C1 C7 129.65(15) . . ?
N1 C1 C7 122.70(15) . . ?
C1 C2 C3 108.12(14) . . ?
C1 C2 C6 125.11(14) . . ?
C3 C2 C6 126.65(15) . . ?
C4 C3 C2 106.83(14) . . ?
C4 C3 C10 126.07(14) . . ?
C2 C3 C10 127.02(15) . . ?
N1 C4 C3 108.16(13) . . ?
N1 C4 C5 121.80(14) . . ?
C3 C4 C5 129.31(15) . . ?
C12 C5 C9 106.62(15) . . ?
C12 C5 C4 129.50(16) . . ?
C9 C5 C4 123.75(15) . . ?
O4 C6 O2 124.41(16) . . ?
O4 C6 C2 124.30(16) . . ?
O2 C6 C2 111.29(15) . . ?
O3 C7 O1 123.04(16) . . ?
O3 C7 C1 126.75(16) . . ?
O1 C7 C1 110.21(15) . . ?
C13 C8 C14 120.93(16) . . ?
C13 C8 N1 120.65(15) . . ?
C14 C8 N1 118.41(15) . . ?
C20 C9 C11 118.72(17) . . ?
C20 C9 C5 134.37(16) . . ?
C11 C9 C5 106.86(15) . . ?
C15 C10 C16 117.85(18) . . ?
C15 C10 C3 120.50(18) . . ?
C16 C10 C3 121.63(17) . . ?
N2 C11 C00R 130.62(18) . . ?
N2 C11 C9 107.17(15) . . ?
C00R C11 C9 122.16(19) . . ?
C5 C12 N2 109.90(17) . . ?
C5 C12 H12 125.1 . . ?
N2 C12 H12 125.1 . . ?
C8 C13 C17 118.97(18) . . ?
C8 C13 H13 120.5 . . ?
C17 C13 H13 120.5 . . ?
C8 C14 C19 119.10(18) . . ?
C8 C14 H14 120.4 . . ?
C19 C14 H14 120.4 . . ?
C10 C15 C00W 120.5(2) . . ?
C10 C15 H15 119.8 . . ?
C00W C15 H15 119.8 . . ?
C00V C16 C10 121.3(2) . . ?
C00V C16 H16 119.3 . . ?
C10 C16 H16 119.3 . . ?
C18 C17 C13 121.55(19) . . ?
C18 C17 H17 119.2 . . ?
C13 C17 H17 119.2 . . ?
C19 C18 C17 117.64(18) . . ?
C19 C18 C00Y 120.8(2) . . ?
C17 C18 C00Y 121.6(2) . . ?
C18 C19 C14 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C00X C20 C9 118.6(2) . . ?
C00X C20 H20 120.7 . . ?
C9 C20 H20 120.7 . . ?
C00U C00R C11 117.4(2) . . ?
C00U C00R H00R 121.3 . . ?
C11 C00R H00R 121.3 . . ?
C00V C00S C00W 120.2(2) . . ?
C00V C00S H00S 119.9 . . ?
C00W C00S H00S 119.9 . . ?
O1 C00T H00A 109.5 . . ?
O1 C00T H00B 109.5 . . ?
H00A C00T H00B 109.5 . . ?
O1 C00T H00C 109.5 . . ?
H00A C00T H00C 109.5 . . ?
H00B C00T H00C 109.5 . . ?
C00R C00U C00X 121.6(2) . . ?
C00R C00U H00U 119.2 . . ?
C00X C00U H00U 119.2 . . ?
C00S C00V C16 120.2(3) . . ?
C00S C00V H00V 119.9 . . ?
C16 C00V H00V 119.9 . . ?
C00S C00W C15 119.9(3) . . ?
C00S C00W H00W 120.1 . . ?
C15 C00W H00W 120.1 . . ?
C20 C00X C00U 121.5(2) . . ?
C20 C00X H00X 119.2 . . ?
C00U C00X H00X 119.2 . . ?
C18 C00Y H00D 109.5 . . ?
C18 C00Y H00E 109.5 . . ?
H00D C00Y H00E 109.5 . . ?
C18 C00Y H00F 109.5 . . ?
H00D C00Y H00F 109.5 . . ?
H00E C00Y H00F 109.5 . . ?
O2 C00Z H00G 109.5 . . ?
O2 C00Z H00H 109.5 . . ?
H00G C00Z H00H 109.5 . . ?
O2 C00Z H00I 109.5 . . ?
H00G C00Z H00I 109.5 . . ?
H00H C00Z H00I 109.5 . . ?
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 C7 1.336(2) . ?
O1 C00T 1.436(2) . ?
O2 C6 1.329(2) . ?
O2 C00Z 1.449(3) . ?
N1 C4 1.370(2) . ?
N1 C1 1.384(2) . ?
N1 C8 1.447(2) . ?
O3 C7 1.205(2) . ?
O4 C6 1.193(2) . ?
N2 C12 1.367(2) . ?
N2 C11 1.371(3) . ?
N2 H1 0.88(3) . ?
C1 C2 1.379(2) . ?
C1 C7 1.456(2) . ?
C2 C3 1.413(2) . ?
C2 C6 1.492(2) . ?
C3 C4 1.393(2) . ?
C3 C10 1.480(2) . ?
C4 C5 1.471(2) . ?
C5 C12 1.359(2) . ?
C5 C9 1.437(2) . ?
C8 C13 1.362(3) . ?
C8 C14 1.375(3) . ?
C9 C20 1.395(3) . ?
C9 C11 1.409(2) . ?
C10 C15 1.388(3) . ?
C10 C16 1.391(3) . ?
C11 C00R 1.394(3) . ?
C12 H12 0.9300 . ?
C13 C17 1.392(3) . ?
C13 H13 0.9300 . ?
C14 C19 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C00W 1.396(3) . ?
C15 H15 0.9300 . ?
C16 C00V 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 C00Y 1.515(3) . ?
C19 H19 0.9300 . ?
C20 C00X 1.379(3) . ?
C20 H20 0.9300 . ?
C00R C00U 1.364(4) . ?
C00R H00R 0.9300 . ?
C00S C00V 1.357(4) . ?
C00S C00W 1.380(4) . ?
C00S H00S 0.9300 . ?
C00T H00A 0.9600 . ?
C00T H00B 0.9600 . ?
C00T H00C 0.9600 . ?
C00U C00X 1.388(4) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Y H00D 0.9600 . ?
C00Y H00E 0.9600 . ?
C00Y H00F 0.9600 . ?
C00Z H00G 0.9600 . ?
C00Z H00H 0.9600 . ?
C00Z H00I 0.9600 . ?
