#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/80/7228078.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_7228078
loop_
_publ_author_name
'Chen, Jing-Min'
'Hou, Yi-Xuan'
'Zhou, Qian-Kun'
'Zhang, Hao'
'Liu, Dong'
_publ_section_title
;
 Regiospecific [2+2] photocycloadditions of an unsymmetrical olefin in the
 solid state based on metal-mediated assemblies
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00573C
_journal_year                    2017
_chemical_formula_moiety         'C24 H20 N4'
_chemical_formula_sum            'C24 H20 N4'
_chemical_formula_weight         364.44
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_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
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.112(2)
_cell_length_b                   16.437(3)
_cell_length_c                   19.547(4)
_cell_measurement_reflns_used    70182
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.551
_cell_measurement_theta_min      3.041
_cell_volume                     3891.5(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL and Diamond'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            68757
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0505
_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)+(0.0628P)²+1.3653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                3384
_reflns_number_total             4466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00573c2.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7228078
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 1.00452(13) 0.50173(11) 0.78495(8) 0.0629(4) Uani 1 1 d .
N2 N 0.87084(12) 0.47120(9) 0.40624(7) 0.0541(3) Uani 1 1 d .
N3 N 0.81832(18) 0.71043(10) 0.85378(7) 0.0745(5) Uani 1 1 d .
N4 N 0.48928(15) 0.68199(14) 0.45741(9) 0.0795(6) Uani 1 1 d .
C1 C 0.94891(17) 0.44940(12) 0.82347(9) 0.0637(5) Uani 1 1 d .
H1 H 0.9856 0.4253 0.8607 0.076 Uiso 1 1 calc R
C2 C 0.84169(17) 0.42874(13) 0.81205(11) 0.0699(5) Uani 1 1 d .
H2 H 0.8056 0.3912 0.8407 0.084 Uiso 1 1 calc R
C3 C 0.78675(14) 0.46397(11) 0.75757(9) 0.0569(4) Uani 1 1 d .
H3 H 0.7129 0.4501 0.7486 0.068 Uiso 1 1 calc R
C4 C 0.84053(12) 0.51944(9) 0.71642(7) 0.0397(3) Uani 1 1 d .
C5 C 0.94981(13) 0.53541(10) 0.73251(8) 0.0499(4) Uani 1 1 d .
H5 H 0.9883 0.5725 0.7047 0.060 Uiso 1 1 calc R
C6 C 0.77856(11) 0.56365(9) 0.66125(7) 0.0387(3) Uani 1 1 d .
H6 H 0.7168 0.5289 0.6455 0.046 Uiso 1 1 calc R
C7 C 0.83741(11) 0.59945(9) 0.59807(7) 0.0380(3) Uani 1 1 d .
H7 H 0.9126 0.6166 0.6118 0.046 Uiso 1 1 calc R
C8 C 0.84573(11) 0.55331(9) 0.53194(7) 0.0393(3) Uani 1 1 d .
C9 C 0.91040(14) 0.58395(10) 0.47968(7) 0.0482(4) Uani 1 1 d .
H9 H 0.9475 0.6337 0.4853 0.058 Uiso 1 1 calc R
C10 C 0.92031(15) 0.54134(10) 0.41924(8) 0.0544(4) Uani 1 1 d .
H10 H 0.9653 0.5636 0.3849 0.065 Uiso 1 1 calc R
C11 C 0.80756(15) 0.44262(12) 0.45614(9) 0.0589(4) Uani 1 1 d .
H11 H 0.7701 0.3934 0.4485 0.071 Uiso 1 1 calc R
C12 C 0.79293(14) 0.48067(11) 0.51901(8) 0.0545(4) Uani 1 1 d .
H12 H 0.7473 0.4570 0.5525 0.065 Uiso 1 1 calc R
C13 C 0.9044(2) 0.75845(12) 0.84149(10) 0.0770(6) Uani 1 1 d .
H13 H 0.9434 0.7796 0.8791 0.092 Uiso 1 1 calc R
C14 C 0.9393(2) 0.77871(12) 0.77716(10) 0.0741(6) Uani 1 1 d .
H14 H 1.0002 0.8134 0.7710 0.089 Uiso 1 1 calc R
C15 C 0.88366(17) 0.74736(11) 0.72155(8) 0.0600(5) Uani 1 1 d .
H15 H 0.9060 0.7608 0.6769 0.072 Uiso 1 1 calc R
C16 C 0.79486(14) 0.69611(9) 0.73178(7) 0.0445(3) Uani 1 1 d .
C17 C 0.76600(17) 0.68076(11) 0.79959(8) 0.0592(4) Uani 1 1 d .
H17 H 0.7049 0.6468 0.8075 0.071 Uiso 1 1 calc R
C18 C 0.73236(12) 0.65187(9) 0.67688(7) 0.0428(3) Uani 1 1 d .
H18 H 0.6519 0.6513 0.6859 0.051 Uiso 1 1 calc R
C19 C 0.75871(12) 0.67592(9) 0.60180(7) 0.0420(3) Uani 1 1 d .
H19 H 0.8006 0.7276 0.5993 0.050 Uiso 1 1 calc R
C20 C 0.66319(13) 0.67504(10) 0.55274(8) 0.0459(3) Uani 1 1 d .
C21 C 0.66905(16) 0.72148(11) 0.49380(9) 0.0601(4) Uani 1 1 d .
H21 H 0.7329 0.7520 0.4843 0.072 Uiso 1 1 calc R
C22 C 0.58163(19) 0.72291(14) 0.44927(11) 0.0755(6) Uani 1 1 d .
H22 H 0.5882 0.7556 0.4100 0.091 Uiso 1 1 calc R
C23 C 0.48545(17) 0.63511(17) 0.51272(12) 0.0816(7) Uani 1 1 d .
H23 H 0.4219 0.6033 0.5193 0.098 Uiso 1 1 calc R
C24 C 0.56809(15) 0.62967(14) 0.56134(10) 0.0660(5) Uani 1 1 d .
H24 H 0.5597 0.5956 0.5996 0.079 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
C1 N1 C5 116.79(16)
C10 N2 C11 115.39(14)
C17 N3 C13 116.64(16)
C22 N4 C23 115.14(17)
N1 C1 C2 123.58(17)
N1 C1 H1 118.2
C2 C1 H1 118.2
C1 C2 C3 118.76(17)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 119.91(16)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 116.36(14)
C3 C4 C6 120.18(14)
C5 C4 C6 123.29(13)
N1 C5 C4 124.59(15)
N1 C5 H5 117.7
C4 C5 H5 117.7
C4 C6 C7 121.92(12)
C4 C6 C18 118.76(11)
C7 C6 C18 88.19(10)
C4 C6 H6 108.7
C7 C6 H6 108.7
C18 C6 H6 108.7
C8 C7 C6 121.82(12)
C8 C7 C19 118.82(11)
C6 C7 C19 89.30(10)
C8 C7 H7 108.4
C6 C7 H7 108.4
C19 C7 H7 108.4
C12 C8 C9 116.30(14)
C12 C8 C7 124.36(13)
C9 C8 C7 119.34(13)
C10 C9 C8 119.84(15)
C10 C9 H9 120.1
C8 C9 H9 120.1
N2 C10 C9 124.58(16)
N2 C10 H10 117.7
C9 C10 H10 117.7
N2 C11 C12 124.35(16)
N2 C11 H11 117.8
C12 C11 H11 117.8
C8 C12 C11 119.53(15)
C8 C12 H12 120.2
C11 C12 H12 120.2
N3 C13 C14 123.59(18)
N3 C13 H13 118.2
C14 C13 H13 118.2
C13 C14 C15 118.8(2)
C13 C14 H14 120.6
C15 C14 H14 120.6
C14 C15 C16 119.65(16)
C14 C15 H15 120.2
C16 C15 H15 120.2
C15 C16 C17 116.33(15)
C15 C16 C18 125.78(13)
C17 C16 C18 117.75(15)
N3 C17 C16 124.94(18)
N3 C17 H17 117.5
C16 C17 H17 117.5
C16 C18 C19 116.66(12)
C16 C18 C6 113.78(12)
C19 C18 C6 88.75(10)
C16 C18 H18 111.9
C19 C18 H18 111.9
C6 C18 H18 111.9
C20 C19 C18 116.25(12)
C20 C19 C7 115.31(12)
C18 C19 C7 88.00(10)
C20 C19 H19 111.8
C18 C19 H19 111.8
C7 C19 H19 111.8
C24 C20 C21 116.20(16)
C24 C20 C19 124.69(15)
C21 C20 C19 119.11(15)
C22 C21 C20 119.90(19)
C22 C21 H21 120.1
C20 C21 H21 120.1
N4 C22 C21 124.9(2)
N4 C22 H22 117.6
C21 C22 H22 117.6
N4 C23 C24 124.9(2)
N4 C23 H23 117.6
C24 C23 H23 117.6
C20 C24 C23 118.98(19)
C20 C24 H24 120.5
C23 C24 H24 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.327(2)
N1 C5 1.340(2)
N2 C10 1.324(2)
N2 C11 1.327(2)
N3 C17 1.327(2)
N3 C13 1.329(3)
N4 C22 1.315(3)
N4 C23 1.328(3)
C1 C2 1.361(3)
C1 H1 0.9400
C2 C3 1.383(3)
C2 H2 0.9400
C3 C4 1.379(2)
C3 H3 0.9400
C4 C5 1.386(2)
C4 C6 1.501(2)
C5 H5 0.9400
C6 C7 1.5427(18)
C6 C18 1.584(2)
C6 H6 0.9900
C7 C8 1.5021(19)
C7 C19 1.579(2)
C7 H7 0.9900
C8 C12 1.378(2)
C8 C9 1.382(2)
C9 C10 1.379(2)
C9 H9 0.9400
C10 H10 0.9400
C11 C12 1.390(2)
C11 H11 0.9400
C12 H12 0.9400
C13 C14 1.368(3)
C13 H13 0.9400
C14 C15 1.379(2)
C14 H14 0.9400
C15 C16 1.381(2)
C15 H15 0.9400
C16 C17 1.394(2)
C16 C18 1.501(2)
C17 H17 0.9400
C18 C19 1.5532(19)
C18 H18 0.9900
C19 C20 1.503(2)
C19 H19 0.9900
C20 C24 1.382(3)
C20 C21 1.384(2)
C21 C22 1.371(3)
C21 H21 0.9400
C22 H22 0.9400
C23 C24 1.383(3)
C23 H23 0.9400
C24 H24 0.9400
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11228131
