#------------------------------------------------------------------------------
#$Date: 2020-05-01 23:33:46 +0300 (Fri, 01 May 2020) $
#$Revision: 251382 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038320.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_4038320
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            'C33 H27 Cl N O5'
_chemical_formula_weight         553.01
_chemical_name_common            'naphthalyl pyrrole'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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                 117.223(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0780(19)
_cell_length_b                   21.490(3)
_cell_length_c                   12.2066(18)
_cell_measurement_reflns_used    9385
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.67
_cell_volume                     2817.4(7)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            74640
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.178
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0589
_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)+(0.0916P)²+1.8762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                4203
_reflns_number_total             4949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00712_si_003.cif
_cod_data_source_block           ysr104a_0m
_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_cell_volume        2817.3(7)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4038320
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.37714(9) 0.16049(4) 0.54828(9) 0.0797(3) Uani 1 1 d . . .
O5 O 0.80808(19) 0.38801(10) 0.58898(18) 0.0666(6) Uani 1 1 d . . .
O3 O 0.5259(2) 0.59158(9) 0.2263(2) 0.0745(7) Uani 1 1 d . . .
N1 N 0.60144(18) 0.46319(9) 0.29781(18) 0.0433(5) Uani 1 1 d . . .
O4 O 0.34102(18) 0.56694(9) 0.2128(2) 0.0674(6) Uani 1 1 d . . .
O1 O 0.3086(2) 0.49910(11) 0.4073(2) 0.0755(6) Uani 1 1 d . . .
O2 O 0.23121(18) 0.42236(10) 0.2708(2) 0.0742(6) Uani 1 1 d . . .
C2 C 0.4361(2) 0.45011(10) 0.3306(2) 0.0400(5) Uani 1 1 d . . .
C1 C 0.4940(2) 0.49139(10) 0.2866(2) 0.0421(5) Uani 1 1 d . . .
C3 C 0.5080(2) 0.39537(10) 0.3668(2) 0.0381(5) Uani 1 1 d . . .
C15 C 0.4795(2) 0.33796(10) 0.4152(2) 0.0402(5) Uani 1 1 d . . .
C5 C 0.7180(2) 0.36318(10) 0.3742(2) 0.0423(5) Uani 1 1 d . . .
C31 C 0.3197(2) 0.46142(11) 0.3415(2) 0.0473(6) Uani 1 1 d . . .
C21 C 0.6853(2) 0.48699(10) 0.2524(2) 0.0437(6) Uani 1 1 d . . .
C4 C 0.6105(2) 0.40497(10) 0.3465(2) 0.0409(5) Uani 1 1 d . . .
C28 C 0.4585(2) 0.55506(11) 0.2387(2) 0.0463(6) Uani 1 1 d . . .
C14 C 0.8082(2) 0.35625(11) 0.4930(2) 0.0439(6) Uani 1 1 d . . .
C13 C 0.9104(2) 0.31452(11) 0.5235(2) 0.0484(6) Uani 1 1 d . . .
C16 C 0.4358(3) 0.33965(11) 0.5027(2) 0.0500(6) Uani 1 1 d . . .
H16 H 0.4276 0.3778 0.5341 0.060 Uiso 1 1 calc R . .
C6 C 0.7275(3) 0.32867(12) 0.2793(3) 0.0528(6) Uani 1 1 d . . .
H6 H 0.6674 0.3336 0.1980 0.063 Uiso 1 1 calc R . .
C20 C 0.4913(3) 0.28003(11) 0.3705(3) 0.0526(6) Uani 1 1 d . . .
H20 H 0.5208 0.2777 0.3123 0.063 Uiso 1 1 calc R . .
C8 C 0.9167(3) 0.28058(12) 0.4282(3) 0.0522(6) Uani 1 1 d . . .
C27 C 0.6502(3) 0.48374(13) 0.1290(3) 0.0548(7) Uani 1 1 d . . .
H27 H 0.5748 0.4655 0.0756 0.066 Uiso 1 1 calc R . .
C17 C 0.4044(3) 0.28590(12) 0.5439(3) 0.0544(7) Uani 1 1 d . . .
H17 H 0.3752 0.2878 0.6023 0.065 Uiso 1 1 calc R . .
C7 C 0.8239(3) 0.28853(14) 0.3066(3) 0.0618(8) Uani 1 1 d . . .
H7 H 0.8282 0.2660 0.2435 0.074 Uiso 1 1 calc R . .
C26 C 0.7276(3) 0.50780(14) 0.0842(3) 0.0606(7) Uani 1 1 d . . .
H26 H 0.7024 0.5063 -0.0001 0.073 Uiso 1 1 calc R . .
C24 C 0.8405(3) 0.53376(13) 0.1606(3) 0.0577(7) Uani 1 1 d . . .
C19 C 0.4601(3) 0.22591(12) 0.4109(3) 0.0564(7) Uani 1 1 d . . .
H19 H 0.4683 0.1875 0.3801 0.068 Uiso 1 1 calc R . .
C22 C 0.7987(3) 0.51117(14) 0.3313(3) 0.0606(7) Uani 1 1 d . . .
H22 H 0.8238 0.5121 0.4155 0.073 Uiso 1 1 calc R . .
C18 C 0.4169(2) 0.22940(11) 0.4971(3) 0.0494(6) Uani 1 1 d . . .
C9 C 1.0196(3) 0.23875(15) 0.4613(4) 0.0723(9) Uani 1 1 d . . .
H9 H 1.0260 0.2155 0.4001 0.087 Uiso 1 1 calc R . .
C23 C 0.8761(3) 0.53430(15) 0.2852(3) 0.0692(8) Uani 1 1 d . . .
H23 H 0.9534 0.5505 0.3393 0.083 Uiso 1 1 calc R . .
C12 C 1.0041(3) 0.30703(16) 0.6451(3) 0.0676(8) Uani 1 1 d . . .
H12 H 1.0003 0.3296 0.7082 0.081 Uiso 1 1 calc R . .
C25 C 0.9274(3) 0.56193(17) 0.1064(3) 0.0770(9) Uani 1 1 d . . .
H25A H 0.8990 0.6029 0.0746 0.116 Uiso 1 1 calc R . .
H25B H 0.9240 0.5357 0.0413 0.116 Uiso 1 1 calc R . .
H25C H 1.0117 0.5642 0.1706 0.116 Uiso 1 1 calc R . .
C29 C 0.2956(3) 0.63017(14) 0.1753(3) 0.0711(9) Uani 1 1 d . . .
H29A H 0.3645 0.6591 0.2120 0.085 Uiso 1 1 calc R . .
H29B H 0.2358 0.6405 0.2050 0.085 Uiso 1 1 calc R . .
C10 C 1.1070(3) 0.23236(18) 0.5789(4) 0.0829(11) Uani 1 1 d . . .
H10 H 1.1723 0.2045 0.5984 0.100 Uiso 1 1 calc R . .
C11 C 1.1002(3) 0.26721(18) 0.6715(4) 0.0839(10) Uani 1 1 d . . .
H11 H 1.1620 0.2632 0.7523 0.101 Uiso 1 1 calc R . .
C30 C 0.2361(5) 0.6366(2) 0.0400(4) 0.1086(16) Uani 1 1 d . . .
H30A H 0.2953 0.6268 0.0106 0.163 Uiso 1 1 calc R . .
H30B H 0.2076 0.6786 0.0177 0.163 Uiso 1 1 calc R . .
H30C H 0.1666 0.6086 0.0037 0.163 Uiso 1 1 calc R . .
C32 C 0.1126(4) 0.4267(2) 0.2750(6) 0.128(2) Uani 1 1 d . . .
H32A H 0.1052 0.4682 0.3022 0.153 Uiso 1 1 calc R . .
H32B H 0.0459 0.4215 0.1921 0.153 Uiso 1 1 calc R . .
C33 C 0.0964(7) 0.3857(3) 0.3479(9) 0.184(4) Uani 1 1 d . . .
H33A H 0.0980 0.3444 0.3189 0.276 Uiso 1 1 calc R . .
H33B H 0.0176 0.3930 0.3469 0.276 Uiso 1 1 calc R . .
H33C H 0.1620 0.3902 0.4304 0.276 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'
Cl Cl 0.1484 0.1585 '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
C4 N1 C1 109.20(19) . . ?
C4 N1 C21 123.87(19) . . ?
C1 N1 C21 126.54(19) . . ?
C28 O4 C29 117.5(2) . . ?
C31 O2 C32 116.8(3) . . ?
C1 C2 C3 108.0(2) . . ?
C1 C2 C31 126.6(2) . . ?
C3 C2 C31 125.4(2) . . ?
C2 C1 N1 107.43(19) . . ?
C2 C1 C28 130.1(2) . . ?
N1 C1 C28 122.4(2) . . ?
C4 C3 C2 107.0(2) . . ?
C4 C3 C15 126.0(2) . . ?
C2 C3 C15 127.0(2) . . ?
C16 C15 C20 117.8(2) . . ?
C16 C15 C3 121.7(2) . . ?
C20 C15 C3 120.5(2) . . ?
C14 C5 C6 119.0(2) . . ?
C14 C5 C4 119.8(2) . . ?
C6 C5 C4 121.2(2) . . ?
O1 C31 O2 124.4(2) . . ?
O1 C31 C2 125.0(2) . . ?
O2 C31 C2 110.6(2) . . ?
C22 C21 C27 120.1(2) . . ?
C22 C21 N1 121.0(2) . . ?
C27 C21 N1 119.0(2) . . ?
N1 C4 C3 108.3(2) . . ?
N1 C4 C5 122.7(2) . . ?
C3 C4 C5 129.0(2) . . ?
O3 C28 O4 124.1(2) . . ?
O3 C28 C1 124.9(2) . . ?
O4 C28 C1 111.0(2) . . ?
O5 C14 C5 123.1(2) . . ?
O5 C14 C13 115.6(2) . . ?
C5 C14 C13 121.3(2) . . ?
C8 C13 C12 119.5(2) . . ?
C8 C13 C14 118.5(2) . . ?
C12 C13 C14 121.9(2) . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C7 C8 C13 119.6(2) . . ?
C7 C8 C9 123.0(3) . . ?
C13 C8 C9 117.4(3) . . ?
C21 C27 C26 119.5(3) . . ?
C21 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C24 C26 C27 121.8(3) . . ?
C24 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C24 C23 117.7(3) . . ?
C26 C24 C25 120.8(3) . . ?
C23 C24 C25 121.5(3) . . ?
C18 C19 C20 119.3(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C22 C23 119.8(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 Cl1 119.2(2) . . ?
C17 C18 Cl1 119.7(2) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C29 C30 111.0(3) . . ?
O4 C29 H29A 109.4 . . ?
C30 C29 H29A 109.4 . . ?
O4 C29 H29B 109.4 . . ?
C30 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C33 C32 O2 115.4(5) . . ?
C33 C32 H32A 108.4 . . ?
O2 C32 H32A 108.4 . . ?
C33 C32 H32B 108.4 . . ?
O2 C32 H32B 108.4 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
Cl1 C18 1.757(3) . ?
O5 C14 1.356(3) . ?
O3 C28 1.189(3) . ?
N1 C4 1.368(3) . ?
N1 C1 1.381(3) . ?
N1 C21 1.452(3) . ?
O4 C28 1.330(3) . ?
O4 C29 1.458(3) . ?
O1 C31 1.191(3) . ?
O2 C31 1.322(3) . ?
O2 C32 1.460(4) . ?
C2 C1 1.381(3) . ?
C2 C3 1.408(3) . ?
C2 C31 1.491(3) . ?
C1 C28 1.472(3) . ?
C3 C4 1.384(3) . ?
C3 C15 1.475(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.392(3) . ?
C5 C14 1.366(4) . ?
C5 C6 1.424(3) . ?
C5 C4 1.485(3) . ?
C21 C22 1.366(4) . ?
C21 C27 1.367(4) . ?
C14 C13 1.431(3) . ?
C13 C8 1.404(4) . ?
C13 C12 1.405(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C6 C7 1.362(4) . ?
C6 H6 0.9300 . ?
C20 C19 1.381(4) . ?
C20 H20 0.9300 . ?
C8 C7 1.403(4) . ?
C8 C9 1.434(4) . ?
C27 C26 1.381(4) . ?
C27 H27 0.9300 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C7 H7 0.9300 . ?
C26 C24 1.370(4) . ?
C26 H26 0.9300 . ?
C24 C23 1.379(4) . ?
C24 C25 1.594(4) . ?
C19 C18 1.374(4) . ?
C19 H19 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C9 C10 1.345(5) . ?
C9 H9 0.9300 . ?
C23 H23 0.9300 . ?
C12 C11 1.356(4) . ?
C12 H12 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C29 C30 1.476(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C10 C11 1.389(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C32 C33 1.328(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
