#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:21:47 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267038 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128383.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_7128383
loop_
_publ_author_name
'Changmai, Sumi'
'Sultana, Sabera'
'Sarma, Bipul'
'Gogoi, Sanjib'
_publ_section_title
;
 Pd(II)-Catalyzed alkyne annulation through allylic isomerization:
 synthesis of spiro-cyclopentadiene pyrazolones.
;
_journal_issue                   49
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6027
_journal_page_last               6030
_journal_paper_doi               10.1039/d1cc02155a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C38 H28 N2 O'
_chemical_formula_weight         528.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-04-22 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6306(8)
_cell_length_b                   15.1263(11)
_cell_length_c                   17.9884(14)
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.00
_cell_measurement_theta_min      2.26
_cell_volume                     2892.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            68291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.225
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0517
_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)+(0.0658P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3622
_reflns_number_total             5081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02155a2.cif
_cod_data_source_block           BS_132_Pure1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7128382--7128383.cif.'
_cod_database_code               7128383
_shelx_shelxl_version_number     2016/6
_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+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_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
O1 O 0.5336(3) 0.70778(18) 0.25232(15) 0.0549(7) Uani 1 1 d . . . . .
N2 N 0.7687(3) 0.78507(19) 0.13260(18) 0.0481(8) Uani 1 1 d . . . . .
N1 N 0.6432(3) 0.7635(2) 0.15146(16) 0.0459(8) Uani 1 1 d . . . . .
C7 C 0.6310(4) 0.7309(2) 0.2228(2) 0.0417(9) Uani 1 1 d . . . . .
C19 C 0.9273(3) 0.5966(2) 0.4038(2) 0.0419(9) Uani 1 1 d . . . . .
C18 C 0.8603(3) 0.6619(2) 0.3564(2) 0.0397(9) Uani 1 1 d . . . . .
C12 C 0.7875(3) 0.5587(2) 0.2518(2) 0.0421(9) Uani 1 1 d . . . . .
C11 C 0.8094(4) 0.6456(2) 0.2886(2) 0.0414(9) Uani 1 1 d . . . . .
C26 C 0.8893(3) 0.7974(2) 0.4450(2) 0.0404(9) Uani 1 1 d . . . . .
C25 C 0.8455(3) 0.7567(2) 0.37479(19) 0.0387(8) Uani 1 1 d . . . . .
C33 C 0.7590(3) 0.8942(2) 0.3091(2) 0.0432(9) Uani 1 1 d . . . . .
C32 C 0.7852(3) 0.7988(2) 0.3179(2) 0.0403(9) Uani 1 1 d . . . . .
C1 C 0.5435(4) 0.7921(3) 0.1038(2) 0.0472(10) Uani 1 1 d . . . . .
C8 C 0.7643(3) 0.7322(2) 0.2553(2) 0.0407(9) Uani 1 1 d . . . . .
C9 C 0.8392(4) 0.7648(2) 0.1882(2) 0.0446(9) Uani 1 1 d . . . . .
C31 C 0.8063(4) 0.8422(3) 0.4909(2) 0.0523(11) Uani 1 1 d . . . . .
H31 H 0.722969 0.849335 0.476251 0.063 Uiso 1 1 calc R U . . .
C17 C 0.7408(4) 0.4876(2) 0.2928(2) 0.0538(11) Uani 1 1 d . . . . .
H17 H 0.724009 0.494724 0.343208 0.065 Uiso 1 1 calc R U . . .
C38 C 0.6430(4) 0.9251(3) 0.2829(2) 0.0551(11) Uani 1 1 d . . . . .
H38 H 0.578833 0.885180 0.272473 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8098(4) 0.5458(3) 0.1770(2) 0.0505(10) Uani 1 1 d . . . . .
H13 H 0.838894 0.592669 0.148344 0.061 Uiso 1 1 calc R U . . .
C27 C 1.0145(4) 0.7898(3) 0.4673(2) 0.0524(11) Uani 1 1 d . . . . .
H27 H 1.072067 0.761501 0.436513 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7193(4) 0.4063(3) 0.2594(3) 0.0621(12) Uani 1 1 d . . . . .
H16 H 0.688370 0.359420 0.287415 0.075 Uiso 1 1 calc R U . . .
C37 C 0.6231(5) 1.0143(3) 0.2726(3) 0.0673(14) Uani 1 1 d . . . . .
H37 H 0.545508 1.033860 0.255351 0.081 Uiso 1 1 calc R U . . .
C20 C 1.0152(4) 0.5405(3) 0.3721(3) 0.0551(11) Uani 1 1 d . . . . .
H20 H 1.030349 0.543368 0.321279 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7900(4) 0.4648(3) 0.1440(3) 0.0634(12) Uani 1 1 d . . . . .
H14 H 0.807860 0.457164 0.093760 0.076 Uiso 1 1 calc R U . . .
C34 C 0.8522(4) 0.9561(3) 0.3252(2) 0.0571(11) Uani 1 1 d . . . . .
H34 H 0.929948 0.937220 0.342875 0.068 Uiso 1 1 calc R U . . .
C28 C 1.0538(4) 0.8238(3) 0.5346(2) 0.0630(13) Uani 1 1 d . . . . .
H28 H 1.137413 0.817628 0.548989 0.076 Uiso 1 1 calc R U . . .
C24 C 0.9076(4) 0.5911(3) 0.4808(2) 0.0562(11) Uani 1 1 d . . . . .
H24 H 0.849428 0.628192 0.503606 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4370(4) 0.7408(3) 0.0961(2) 0.0606(12) Uani 1 1 d . . . . .
H6 H 0.432155 0.685982 0.119392 0.073 Uiso 1 1 calc R U . . .
C10 C 0.9774(4) 0.7779(3) 0.1874(3) 0.0623(12) Uani 1 1 d . . . . .
H10A H 1.005597 0.784720 0.137016 0.093 Uiso 1 1 calc R U . . .
H10B H 1.017870 0.727551 0.209344 0.093 Uiso 1 1 calc R U . . .
H10C H 0.998262 0.830027 0.215276 0.093 Uiso 1 1 calc R U . . .
C30 C 0.8464(5) 0.8766(3) 0.5588(3) 0.0660(12) Uani 1 1 d . . . . .
H30 H 0.789793 0.906118 0.589315 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7438(4) 0.3952(3) 0.1851(3) 0.0654(13) Uani 1 1 d . . . . .
H15 H 0.729149 0.340780 0.162574 0.078 Uiso 1 1 calc R U . . .
C2 C 0.5514(5) 0.8726(3) 0.0681(3) 0.0710(14) Uani 1 1 d . . . . .
H2 H 0.623187 0.907261 0.072942 0.085 Uiso 1 1 calc R U . . .
C29 C 0.9702(5) 0.8668(3) 0.5807(2) 0.0667(13) Uani 1 1 d . . . . .
H29 H 0.996867 0.889101 0.626278 0.080 Uiso 1 1 calc R U . . .
C21 C 1.0811(5) 0.4800(3) 0.4154(3) 0.0704(14) Uani 1 1 d . . . . .
H21 H 1.138921 0.442116 0.393288 0.085 Uiso 1 1 calc R U . . .
C36 C 0.7158(5) 1.0745(3) 0.2874(3) 0.0686(13) Uani 1 1 d . . . . .
H36 H 0.702107 1.134357 0.278704 0.082 Uiso 1 1 calc R U . . .
C35 C 0.8299(5) 1.0459(3) 0.3152(3) 0.0705(13) Uani 1 1 d . . . . .
H35 H 0.891897 1.086797 0.327298 0.085 Uiso 1 1 calc R U . . .
C22 C 1.0611(5) 0.4763(3) 0.4906(4) 0.0799(16) Uani 1 1 d . . . . .
H22 H 1.106585 0.436609 0.519516 0.096 Uiso 1 1 calc R U . . .
C23 C 0.9744(5) 0.5306(3) 0.5231(3) 0.0737(14) Uani 1 1 d . . . . .
H23 H 0.960119 0.526959 0.573965 0.088 Uiso 1 1 calc R U . . .
C5 C 0.3378(5) 0.7711(4) 0.0536(3) 0.0753(14) Uani 1 1 d . . . . .
H5 H 0.265607 0.736821 0.048767 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3452(6) 0.8513(4) 0.0185(3) 0.0819(16) Uani 1 1 d . . . . .
H4 H 0.278004 0.871686 -0.009863 0.098 Uiso 1 1 calc R U . . .
C3 C 0.4516(6) 0.9014(4) 0.0252(3) 0.0880(17) Uani 1 1 d . . . . .
H3 H 0.457025 0.955349 0.000599 0.106 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
C9 N2 N1 107.9(3) . . ?
C7 N1 N2 113.2(3) . . ?
C7 N1 C1 126.5(3) . . ?
N2 N1 C1 119.1(3) . . ?
O1 C7 N1 126.1(3) . . ?
O1 C7 C8 128.6(3) . . ?
N1 C7 C8 105.2(3) . . ?
C20 C19 C24 118.1(4) . . ?
C20 C19 C18 119.6(4) . . ?
C24 C19 C18 122.3(3) . . ?
C11 C18 C25 109.5(3) . . ?
C11 C18 C19 125.9(3) . . ?
C25 C18 C19 124.5(3) . . ?
C13 C12 C17 117.8(4) . . ?
C13 C12 C11 122.1(3) . . ?
C17 C12 C11 120.0(4) . . ?
C18 C11 C12 128.5(3) . . ?
C18 C11 C8 108.9(3) . . ?
C12 C11 C8 122.4(3) . . ?
C31 C26 C27 118.5(4) . . ?
C31 C26 C25 120.7(3) . . ?
C27 C26 C25 120.7(3) . . ?
C32 C25 C26 126.5(3) . . ?
C32 C25 C18 109.5(3) . . ?
C26 C25 C18 124.1(3) . . ?
C34 C33 C38 118.1(4) . . ?
C34 C33 C32 120.0(3) . . ?
C38 C33 C32 121.9(3) . . ?
C25 C32 C33 128.6(3) . . ?
C25 C32 C8 108.3(3) . . ?
C33 C32 C8 122.5(3) . . ?
C6 C1 C2 120.0(4) . . ?
C6 C1 N1 119.9(4) . . ?
C2 C1 N1 120.0(4) . . ?
C11 C8 C32 103.4(3) . . ?
C11 C8 C9 115.2(3) . . ?
C32 C8 C9 107.1(3) . . ?
C11 C8 C7 115.5(3) . . ?
C32 C8 C7 115.1(3) . . ?
C9 C8 C7 100.6(3) . . ?
N2 C9 C10 122.5(4) . . ?
N2 C9 C8 112.8(3) . . ?
C10 C9 C8 124.6(3) . . ?
C26 C31 C30 120.6(4) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C16 C17 C12 120.9(4) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C37 C38 C33 120.5(4) . . ?
C37 C38 H38 119.8 . . ?
C33 C38 H38 119.8 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C28 C27 C26 120.7(4) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C36 C37 C38 121.0(4) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C19 C20 C21 120.9(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C33 C34 C35 120.5(4) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C27 C28 C29 120.5(4) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C1 C6 C5 119.7(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C29 C30 C31 120.2(4) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C28 C29 C30 119.5(4) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C37 C36 C35 119.6(4) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C35 C34 120.2(4) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.6(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
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 1.215(4) . ?
N2 C9 1.288(5) . ?
N2 N1 1.414(5) . ?
N1 C7 1.381(5) . ?
N1 C1 1.430(5) . ?
C7 C8 1.534(5) . ?
C19 C20 1.385(5) . ?
C19 C24 1.404(5) . ?
C19 C18 1.486(5) . ?
C18 C11 1.356(5) . ?
C18 C25 1.482(5) . ?
C12 C13 1.380(5) . ?
C12 C17 1.396(5) . ?
C12 C11 1.490(5) . ?
C11 C8 1.518(5) . ?
C26 C31 1.384(5) . ?
C26 C27 1.395(5) . ?
C26 C25 1.481(5) . ?
C25 C32 1.365(5) . ?
C33 C34 1.395(5) . ?
C33 C38 1.401(5) . ?
C33 C32 1.478(5) . ?
C32 C8 1.526(5) . ?
C1 C6 1.380(6) . ?
C1 C2 1.379(6) . ?
C8 C9 1.527(5) . ?
C9 C10 1.483(5) . ?
C31 C30 1.394(6) . ?
C31 H31 0.9300 . ?
C17 C16 1.387(6) . ?
C17 H17 0.9300 . ?
C38 C37 1.378(6) . ?
C38 H38 0.9300 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9300 . ?
C27 C28 1.380(5) . ?
C27 H27 0.9300 . ?
C16 C15 1.373(6) . ?
C16 H16 0.9300 . ?
C37 C36 1.368(7) . ?
C37 H37 0.9300 . ?
C20 C21 1.391(6) . ?
C20 H20 0.9300 . ?
C14 C15 1.378(6) . ?
C14 H14 0.9300 . ?
C34 C35 1.390(6) . ?
C34 H34 0.9300 . ?
C28 C29 1.380(6) . ?
C28 H28 0.9300 . ?
C24 C23 1.385(6) . ?
C24 H24 0.9300 . ?
C6 C5 1.381(6) . ?
C6 H6 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C30 C29 1.381(7) . ?
C30 H30 0.9300 . ?
C15 H15 0.9300 . ?
C2 C3 1.382(7) . ?
C2 H2 0.9300 . ?
C29 H29 0.9300 . ?
C21 C22 1.370(7) . ?
C21 H21 0.9300 . ?
C36 C35 1.382(7) . ?
C36 H36 0.9300 . ?
C35 H35 0.9300 . ?
C22 C23 1.367(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C5 C4 1.371(7) . ?
C5 H5 0.9300 . ?
C4 C3 1.367(8) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
