#------------------------------------------------------------------------------
#$Date: 2022-04-12 03:01:58 +0200 (Tue 12 de Apr de 2022) $
#$Revision: 274466 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/86/7158634.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_7158634
loop_
_publ_author_name
'Ruan, Shuchen'
'Zhou, Chao'
'Li, Laiqiang'
'Wang, Lei'
'Liu, Jie'
'Li, Pinhua'
_publ_section_title
;
 Microwave-accelerated and benzoyl peroxide (BPO) initiated cyclization of
 1,5-enynes having cyano groups with cyclic alkanes under metal-free
 conditions
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00430E
_journal_year                    2022
_chemical_formula_moiety         'C24 H22 N2'
_chemical_formula_sum            'C24 H22 N2'
_chemical_formula_weight         338.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2022-01-07 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.073(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.796(2)
_cell_length_b                   13.651(3)
_cell_length_c                   12.334(2)
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4401
_cell_measurement_theta_min      2.9847
_cell_volume                     1918.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28076
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.093
_diffrn_reflns_theta_min         2.985
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0421
_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)+(0.0489P)²+0.4204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2832
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00430e2.cif
_cod_data_source_block           1
_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/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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        1918.3(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158634
_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.
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_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
C1 C 0.27928(12) 0.52716(10) 0.90492(13) 0.0449(3) Uani 1 1 d . . . . .
C2 C 0.26360(14) 0.42222(12) 0.92461(15) 0.0569(4) Uani 1 1 d . . . . .
C3 C 0.37143(12) 0.53469(10) 0.86531(12) 0.0427(3) Uani 1 1 d . . . . .
C4 C 0.31358(13) 0.58395(11) 1.02913(13) 0.0484(3) Uani 1 1 d . . . . .
H4 H 0.3483 0.5376 1.0971 0.058 Uiso 1 1 calc R U . . .
C5 C 0.39987(12) 0.66879(10) 1.05048(12) 0.0461(3) Uani 1 1 d . . . . .
H5 H 0.4673 0.6410 1.0438 0.055 Uiso 1 1 calc R U . . .
C6 C 0.35259(13) 0.75115(11) 0.95717(13) 0.0500(4) Uani 1 1 d . . . . .
H6A H 0.3265 0.7244 0.8761 0.060 Uiso 1 1 calc R U . . .
H6B H 0.2855 0.7811 0.9607 0.060 Uiso 1 1 calc R U . . .
C7 C 0.44616(15) 0.82853(12) 0.98114(14) 0.0609(4) Uani 1 1 d . . . . .
H7A H 0.5095 0.8000 0.9690 0.073 Uiso 1 1 calc R U . . .
H7B H 0.4126 0.8817 0.9234 0.073 Uiso 1 1 calc R U . . .
C8 C 0.49503(16) 0.86877(13) 1.10948(16) 0.0682(5) Uani 1 1 d . . . . .
H8A H 0.5580 0.9144 1.1234 0.082 Uiso 1 1 calc R U . . .
H8B H 0.4339 0.9041 1.1188 0.082 Uiso 1 1 calc R U . . .
C9 C 0.54112(15) 0.78715(14) 1.20261(15) 0.0695(5) Uani 1 1 d . . . . .
H9A H 0.5674 0.8143 1.2835 0.083 Uiso 1 1 calc R U . . .
H9B H 0.6079 0.7564 1.1992 0.083 Uiso 1 1 calc R U . . .
C10 C 0.44715(15) 0.71080(13) 1.17917(13) 0.0620(4) Uani 1 1 d . . . . .
H10A H 0.3833 0.7403 1.1894 0.074 Uiso 1 1 calc R U . . .
H10B H 0.4797 0.6582 1.2381 0.074 Uiso 1 1 calc R U . . .
C11 C 0.19361(13) 0.61379(11) 1.01246(14) 0.0524(4) Uani 1 1 d . . . . .
C12 C 0.16141(17) 0.64134(13) 1.10155(17) 0.0690(5) Uani 1 1 d . . . . .
H12 H 0.2165 0.6422 1.1832 0.083 Uiso 1 1 calc R U . . .
C13 C 0.04700(19) 0.66732(15) 1.0673(2) 0.0808(6) Uani 1 1 d . . . . .
H13 H 0.0243 0.6847 1.1264 0.097 Uiso 1 1 calc R U . . .
C14 C -0.03428(17) 0.66786(16) 0.9467(2) 0.0840(6) Uani 1 1 d . . . . .
H14 H -0.1110 0.6869 0.9253 0.101 Uiso 1 1 calc R U . . .
C15 C -0.00415(15) 0.64057(14) 0.85685(18) 0.0718(5) Uani 1 1 d . . . . .
H15 H -0.0594 0.6415 0.7753 0.086 Uiso 1 1 calc R U . . .
C16 C 0.11081(13) 0.61163(11) 0.89115(14) 0.0526(4) Uani 1 1 d . . . . .
C17 C 0.16016(12) 0.57063(10) 0.81383(13) 0.0462(3) Uani 1 1 d . . . . .
C18 C 0.11181(12) 0.57094(11) 0.69269(14) 0.0510(4) Uani 1 1 d . . . . .
H18 H 0.0414 0.6051 0.6543 0.061 Uiso 1 1 calc R U . . .
C19 C 0.15202(12) 0.52580(11) 0.60977(13) 0.0503(4) Uani 1 1 d . . . . .
C20 C 0.20298(16) 0.43361(13) 0.62944(16) 0.0682(5) Uani 1 1 d . . . . .
H20 H 0.2126 0.3980 0.6976 0.082 Uiso 1 1 calc R U . . .
C21 C 0.23961(16) 0.39382(16) 0.55007(19) 0.0805(6) Uani 1 1 d . . . . .
H21 H 0.2744 0.3322 0.5657 0.097 Uiso 1 1 calc R U . . .
C22 C 0.22543(16) 0.44345(18) 0.4497(2) 0.0823(6) Uani 1 1 d . . . . .
H22 H 0.2525 0.4170 0.3976 0.099 Uiso 1 1 calc R U . . .
C23 C 0.17068(18) 0.53365(17) 0.42449(18) 0.0811(6) Uani 1 1 d . . . . .
H23 H 0.1583 0.5671 0.3539 0.097 Uiso 1 1 calc R U . . .
C24 C 0.13412(15) 0.57444(13) 0.50473(15) 0.0637(4) Uani 1 1 d . . . . .
H24 H 0.0972 0.6352 0.4874 0.076 Uiso 1 1 calc R U . . .
N1 N 0.24950(17) 0.34242(11) 0.93932(17) 0.0864(5) Uani 1 1 d . . . . .
N2 N 0.44572(11) 0.54161(10) 0.83975(11) 0.0562(3) Uani 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'
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
C3 C1 C2 108.11(11) . . ?
C3 C1 C17 114.01(11) . . ?
C2 C1 C17 109.19(12) . . ?
C3 C1 C4 111.99(11) . . ?
C2 C1 C4 108.18(11) . . ?
C17 C1 C4 105.20(10) . . ?
N1 C2 C1 178.69(17) . . ?
N2 C3 C1 177.05(15) . . ?
C11 C4 C5 115.25(12) . . ?
C11 C4 C1 100.53(11) . . ?
C5 C4 C1 113.19(10) . . ?
C6 C5 C10 109.92(12) . . ?
C6 C5 C4 114.78(12) . . ?
C10 C5 C4 111.96(12) . . ?
C7 C6 C5 111.03(12) . . ?
C8 C7 C6 111.63(13) . . ?
C9 C8 C7 111.03(14) . . ?
C8 C9 C10 111.09(14) . . ?
C9 C10 C5 111.12(13) . . ?
C16 C11 C12 120.24(15) . . ?
C16 C11 C4 111.83(12) . . ?
C12 C11 C4 127.93(15) . . ?
C13 C12 C11 119.01(18) . . ?
C12 C13 C14 120.73(16) . . ?
C13 C14 C15 121.16(17) . . ?
C14 C15 C16 118.42(18) . . ?
C11 C16 C15 120.38(14) . . ?
C11 C16 C17 111.40(13) . . ?
C15 C16 C17 128.11(15) . . ?
C18 C17 C16 127.44(13) . . ?
C18 C17 C1 128.23(12) . . ?
C16 C17 C1 104.32(12) . . ?
C17 C18 C19 130.31(14) . . ?
C24 C19 C20 117.71(15) . . ?
C24 C19 C18 119.33(14) . . ?
C20 C19 C18 122.90(15) . . ?
C21 C20 C19 121.29(18) . . ?
C22 C21 C20 120.5(2) . . ?
C21 C22 C23 119.77(18) . . ?
C22 C23 C24 119.90(19) . . ?
C19 C24 C23 120.70(18) . . ?
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
C1 C3 1.4711(18) . ?
C1 C2 1.482(2) . ?
C1 C17 1.542(2) . ?
C1 C4 1.590(2) . ?
C2 N1 1.132(2) . ?
C3 N2 1.1334(17) . ?
C4 C11 1.509(2) . ?
C4 C5 1.538(2) . ?
C5 C6 1.5234(19) . ?
C5 C10 1.530(2) . ?
C6 C7 1.521(2) . ?
C7 C8 1.516(2) . ?
C8 C9 1.514(3) . ?
C9 C10 1.516(2) . ?
C11 C16 1.385(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.373(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.390(2) . ?
C16 C17 1.4729(19) . ?
C17 C18 1.332(2) . ?
C18 C19 1.473(2) . ?
C19 C24 1.379(2) . ?
C19 C20 1.387(2) . ?
C20 C21 1.375(2) . ?
C21 C22 1.350(3) . ?
C22 C23 1.380(3) . ?
C23 C24 1.389(3) . ?
