#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/90/7239094.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_7239094
loop_
_publ_author_name
'Bej, Ansuman'
'Chakraborty, Amarnath'
'Sarkar, Amitabha'
_publ_section_title
;
 Solvent free, phosphine free Pd-catalyzed annulations of aryl bromides
 with diarylacetylenes
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              15812
_journal_paper_doi               10.1039/c3ra41924j
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C35 H23 N'
_chemical_formula_weight         457.54
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.6655(8)
_cell_length_b                   21.962(2)
_cell_length_c                   32.777(4)
_cell_measurement_reflns_used    6470
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      2.23
_cell_volume                     4798.2(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'MERCURY 2.3'
_computing_publication_material  'ORTEP 3V.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            40482
_diffrn_reflns_theta_full        24.58
_diffrn_reflns_theta_max         24.58
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0453
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                3286
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41924j.txt
_cod_data_source_block           accn1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               7239094
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.0890(2) 0.14328(8) 0.34778(5) 0.0388(4) Uani 1 1 d .
C3 C 0.0801(2) 0.16043(8) 0.24215(5) 0.0274(4) Uani 1 1 d .
H3 H 0.0881 0.2009 0.2503 0.033 Uiso 1 1 calc R
C4 C 0.0782(2) 0.14604(8) 0.20012(5) 0.0246(4) Uani 1 1 d .
C5 C 0.0642(2) 0.08415(8) 0.18834(5) 0.0253(4) Uani 1 1 d .
C22 C 0.1053(2) 0.17593(8) 0.12914(5) 0.0262(4) Uani 1 1 d .
C2 C 0.0703(2) 0.11556(8) 0.27110(5) 0.0279(4) Uani 1 1 d .
C8 C 0.0714(2) 0.06868(8) 0.14620(5) 0.0251(4) Uani 1 1 d .
C15 C 0.1015(2) 0.11364(8) 0.11753(5) 0.0257(4) Uani 1 1 d .
C29 C 0.0926(2) 0.19238(8) 0.16959(5) 0.0256(4) Uani 1 1 d .
C30 C 0.1011(3) 0.25739(8) 0.18223(5) 0.0283(4) Uani 1 1 d .
C16 C 0.1321(3) 0.09724(8) 0.07385(5) 0.0286(4) Uani 1 1 d .
C9 C 0.0381(3) 0.00395(8) 0.13331(5) 0.0280(4) Uani 1 1 d .
C6 C 0.0483(3) 0.03921(8) 0.21921(5) 0.0280(4) Uani 1 1 d .
H6 H 0.0345 -0.0014 0.2118 0.034 Uiso 1 1 calc R
C1 C 0.0794(3) 0.13112(8) 0.31377(6) 0.0295(4) Uani 1 1 d .
C26 C 0.1229(3) 0.30392(9) 0.03106(6) 0.0378(5) Uani 1 1 d .
H26 H 0.1252 0.3307 0.0091 0.045 Uiso 1 1 calc R
C7 C 0.0529(3) 0.05413(8) 0.25949(5) 0.0293(4) Uani 1 1 d .
H7 H 0.0445 0.0239 0.2793 0.035 Uiso 1 1 calc R
C23 C 0.1156(3) 0.22289(8) 0.09614(5) 0.0267(4) Uani 1 1 d .
C24 C 0.2936(3) 0.23425(8) 0.07534(5) 0.0304(4) Uani 1 1 d .
H24 H 0.4109 0.2146 0.0832 0.037 Uiso 1 1 calc R
C31 C 0.2834(3) 0.28699(8) 0.18587(5) 0.0360(5) Uani 1 1 d .
H31 H 0.4012 0.2661 0.1800 0.043 Uiso 1 1 calc R
C27 C -0.0540(3) 0.29352(9) 0.05177(6) 0.0367(5) Uani 1 1 d .
H27 H -0.1709 0.3134 0.0439 0.044 Uiso 1 1 calc R
C13 C 0.1569(3) -0.09219(9) 0.10814(6) 0.0404(5) Uani 1 1 d .
H13 H 0.2621 -0.1168 0.0995 0.048 Uiso 1 1 calc R
C10 C -0.1554(3) -0.01924(8) 0.13332(5) 0.0337(4) Uani 1 1 d .
H10 H -0.2612 0.0053 0.1418 0.040 Uiso 1 1 calc R
C35 C -0.0732(3) 0.28940(9) 0.19100(6) 0.0382(5) Uani 1 1 d .
H35 H -0.1973 0.2704 0.1888 0.046 Uiso 1 1 calc R
C12 C -0.0363(3) -0.11459(9) 0.10842(6) 0.0381(5) Uani 1 1 d .
H12 H -0.0610 -0.1544 0.1001 0.046 Uiso 1 1 calc R
C14 C 0.1941(3) -0.03342(8) 0.12072(5) 0.0341(4) Uani 1 1 d .
H14 H 0.3249 -0.0187 0.1208 0.041 Uiso 1 1 calc R
C28 C -0.0571(3) 0.25331(9) 0.08438(5) 0.0325(4) Uani 1 1 d .
H28 H -0.1761 0.2467 0.0985 0.039 Uiso 1 1 calc R
C20 C 0.0102(4) 0.08075(9) 0.00573(6) 0.0428(5) Uani 1 1 d .
H20 H -0.0954 0.0802 -0.0128 0.051 Uiso 1 1 calc R
C19 C 0.2012(4) 0.06578(8) -0.00699(6) 0.0436(5) Uani 1 1 d .
H19 H 0.2237 0.0549 -0.0340 0.052 Uiso 1 1 calc R
C21 C -0.0246(3) 0.09662(8) 0.04596(6) 0.0360(5) Uani 1 1 d .
H21 H -0.1535 0.1069 0.0544 0.043 Uiso 1 1 calc R
C11 C -0.1933(3) -0.07811(9) 0.12098(6) 0.0386(5) Uani 1 1 d .
H11 H -0.3238 -0.0932 0.1211 0.046 Uiso 1 1 calc R
C18 C 0.3586(3) 0.06680(8) 0.02015(6) 0.0403(5) Uani 1 1 d .
H18 H 0.4874 0.0570 0.0115 0.048 Uiso 1 1 calc R
C25 C 0.2969(3) 0.27461(8) 0.04301(5) 0.0352(5) Uani 1 1 d .
H25 H 0.4164 0.2821 0.0292 0.042 Uiso 1 1 calc R
C33 C 0.1199(4) 0.37855(9) 0.20668(6) 0.0439(5) Uani 1 1 d .
H33 H 0.1261 0.4190 0.2149 0.053 Uiso 1 1 calc R
C17 C 0.3243(3) 0.08254(8) 0.06047(5) 0.0336(4) Uani 1 1 d .
H17 H 0.4308 0.0833 0.0788 0.040 Uiso 1 1 calc R
C34 C -0.0619(3) 0.34989(10) 0.20304(6) 0.0452(5) Uani 1 1 d .
H34 H -0.1791 0.3712 0.2087 0.054 Uiso 1 1 calc R
C32 C 0.2933(4) 0.34698(9) 0.19806(6) 0.0449(5) Uani 1 1 d .
H32 H 0.4172 0.3661 0.2005 0.054 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C3 C4 120.93(17)
C3 C4 C5 118.75(16)
C3 C4 C29 121.48(16)
C5 C4 C29 119.77(15)
C4 C5 C6 118.58(15)
C4 C5 C8 119.45(15)
C6 C5 C8 121.95(16)
C29 C22 C15 120.64(16)
C29 C22 C23 121.21(16)
C15 C22 C23 118.11(15)
C3 C2 C7 120.43(16)
C3 C2 C1 119.99(17)
C7 C2 C1 119.58(16)
C15 C8 C5 119.72(16)
C15 C8 C9 120.57(15)
C5 C8 C9 119.66(15)
C8 C15 C22 120.68(15)
C8 C15 C16 120.13(15)
C22 C15 C16 119.18(15)
C22 C29 C4 119.41(16)
C22 C29 C30 121.19(16)
C4 C29 C30 119.36(15)
C31 C30 C35 118.64(17)
C31 C30 C29 120.55(16)
C35 C30 C29 120.81(16)
C21 C16 C17 118.87(17)
C21 C16 C15 122.12(17)
C17 C16 C15 119.01(15)
C10 C9 C14 118.68(17)
C10 C9 C8 119.06(15)
C14 C9 C8 122.25(16)
C7 C6 C5 121.57(17)
N1 C1 C2 179.18(19)
C27 C26 C25 120.02(18)
C6 C7 C2 119.69(16)
C28 C23 C24 119.06(16)
C28 C23 C22 119.72(15)
C24 C23 C22 121.13(15)
C25 C24 C23 120.31(17)
C32 C31 C30 121.09(19)
C26 C27 C28 119.81(18)
C14 C13 C12 120.05(19)
C11 C10 C9 121.02(18)
C30 C35 C34 119.91(19)
C13 C12 C11 120.20(18)
C13 C14 C9 120.54(18)
C23 C28 C27 120.63(17)
C19 C20 C21 120.19(19)
C18 C19 C20 120.32(18)
C20 C21 C16 120.25(19)
C10 C11 C12 119.51(18)
C19 C18 C17 119.69(19)
C24 C25 C26 120.16(18)
C34 C33 C32 119.54(18)
C18 C17 C16 120.68(18)
C33 C34 C35 120.80(19)
C33 C32 C31 120.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.148(2)
C3 C2 1.370(2)
C3 C4 1.414(2)
C4 C5 1.416(2)
C4 C29 1.430(2)
C5 C6 1.418(2)
C5 C8 1.423(2)
C22 C29 1.377(2)
C22 C15 1.420(2)
C22 C23 1.496(2)
C2 C7 1.407(3)
C2 C1 1.441(2)
C8 C15 1.378(2)
C8 C9 1.500(2)
C15 C16 1.490(2)
C29 C30 1.488(3)
C30 C31 1.384(3)
C30 C35 1.387(3)
C16 C21 1.388(3)
C16 C17 1.392(3)
C9 C10 1.387(3)
C9 C14 1.387(3)
C6 C7 1.361(2)
C26 C27 1.380(3)
C26 C25 1.383(3)
C23 C28 1.385(2)
C23 C24 1.391(2)
C24 C25 1.382(2)
C31 C32 1.378(3)
C27 C28 1.386(3)
C13 C14 1.377(3)
C13 C12 1.378(3)
C10 C11 1.378(3)
C35 C34 1.388(3)
C12 C11 1.381(3)
C20 C19 1.379(3)
C20 C21 1.384(3)
C19 C18 1.375(3)
C18 C17 1.385(3)
C33 C34 1.371(3)
C33 C32 1.377(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340705
