#------------------------------------------------------------------------------
#$Date: 2017-04-14 05:15:31 +0300 (Fri, 14 Apr 2017) $
#$Revision: 195439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/80/7228080.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_7228080
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         '2(C24 H16 N2 O4 Zn), H2 O'
_chemical_formula_sum            'C48 H34 N4 O9 Zn2'
_chemical_formula_weight         941.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 111.23(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.855(3)
_cell_length_b                   11.031(2)
_cell_length_c                   14.277(3)
_cell_measurement_reflns_used    37169
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.560
_cell_measurement_theta_min      3.049
_cell_volume                     2033.9(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    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  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36008
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.245
_exptl_absorpt_correction_T_max  0.8856
_exptl_absorpt_correction_T_min  0.8256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0473P)²+2.7066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                3516
_reflns_number_total             4671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00573c2.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7228080
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Zn1 Zn 0.29166(3) 0.57209(3) 0.67908(3) 0.02726(13) Uani 1 1 d . . .
N1 N 0.3086(2) 0.7295(2) 0.6132(2) 0.0284(6) Uani 1 1 d . . .
N2 N 0.6745(2) 0.9009(2) 0.2351(2) 0.0303(6) Uani 1 1 d . . .
O1 O 0.3983(3) 0.4994(3) 0.7973(3) 0.0701(10) Uani 1 1 d . A .
O2 O 0.4740(6) 0.5038(9) 0.6910(6) 0.066(3) Uani 0.648(19) 1 d P A 1
O2' O 0.5141(10) 0.5747(15) 0.7557(18) 0.085(8) Uani 0.352(19) 1 d P A 2
O3 O 0.7289(3) 0.0632(3) 1.0927(3) 0.0685(10) Uani 1 1 d . . .
O4 O 0.7010(12) -0.0234(7) 0.9599(4) 0.188(9) Uani 0.669(13) 1 d P B 1
O4' O 0.8182(11) 0.0456(12) 1.0045(11) 0.084(7) Uani 0.331(13) 1 d P B 2
C1 C 0.2429(3) 0.8220(3) 0.6025(3) 0.0378(8) Uani 1 1 d . . .
H1 H 0.1980 0.8205 0.6385 0.045 Uiso 1 1 calc R . .
C2 C 0.2386(3) 0.9193(4) 0.5407(3) 0.0438(9) Uani 1 1 d . . .
H2 H 0.1916 0.9829 0.5347 0.053 Uiso 1 1 calc R . .
C3 C 0.3041(3) 0.9221(3) 0.4878(3) 0.0389(8) Uani 1 1 d . . .
H3 H 0.3002 0.9861 0.4431 0.047 Uiso 1 1 calc R . .
C4 C 0.3753(3) 0.8307(3) 0.5007(3) 0.0311(7) Uani 1 1 d . . .
C5 C 0.3744(3) 0.7368(3) 0.5647(3) 0.0334(8) Uani 1 1 d . . .
H5 H 0.4232 0.6744 0.5745 0.040 Uiso 1 1 calc R . .
C6 C 0.4501(3) 0.8253(3) 0.4494(3) 0.0410(9) Uani 1 1 d . . .
H6 H 0.5004 0.7638 0.4697 0.049 Uiso 1 1 calc R . .
C7 C 0.4532(3) 0.8986(3) 0.3776(3) 0.0385(9) Uani 1 1 d . . .
H7 H 0.4019 0.9589 0.3562 0.046 Uiso 1 1 calc R . .
C8 C 0.5283(3) 0.8951(3) 0.3284(3) 0.0330(8) Uani 1 1 d . . .
C9 C 0.5217(3) 0.9782(4) 0.2533(3) 0.0407(9) Uani 1 1 d . . .
H9 H 0.4672 1.0346 0.2329 0.049 Uiso 1 1 calc R . .
C10 C 0.5945(3) 0.9785(4) 0.2086(3) 0.0414(9) Uani 1 1 d . . .
H10 H 0.5879 1.0353 0.1576 0.050 Uiso 1 1 calc R . .
C11 C 0.6801(3) 0.8195(3) 0.3062(3) 0.0369(8) Uani 1 1 d . . .
H11 H 0.7353 0.7639 0.3252 0.044 Uiso 1 1 calc R . .
C12 C 0.6097(3) 0.8132(3) 0.3526(3) 0.0403(9) Uani 1 1 d . . .
H12 H 0.6164 0.7530 0.4011 0.048 Uiso 1 1 calc R . .
C13 C 0.5507(3) 0.3843(3) 0.8421(3) 0.0365(8) Uani 1 1 d . A .
C14 C 0.5295(3) 0.3352(4) 0.9199(3) 0.0445(9) Uani 1 1 d . . .
H14 H 0.4757 0.3679 0.9375 0.053 Uiso 1 1 calc R . .
C15 C 0.5868(3) 0.2359(4) 0.9748(3) 0.0521(11) Uani 1 1 d . . .
H15 H 0.5709 0.2045 1.0287 0.063 Uiso 1 1 calc R . .
C16 C 0.6644(4) 0.1848(4) 0.9513(3) 0.0520(11) Uani 1 1 d . B .
C17 C 0.6938(3) 0.2378(3) 0.8745(3) 0.0462(10) Uani 1 1 d . . .
C18 C 0.6366(3) 0.3406(3) 0.8192(3) 0.0384(8) Uani 1 1 d . . .
C19 C 0.6700(3) 0.3919(4) 0.7453(3) 0.0476(10) Uani 1 1 d . . .
H19 H 0.6337 0.4587 0.7082 0.057 Uiso 1 1 calc R . .
C20 C 0.7526(4) 0.3481(5) 0.7261(4) 0.0636(13) Uani 1 1 d . . .
H20 H 0.7727 0.3842 0.6764 0.076 Uiso 1 1 calc R . .
C21 C 0.8074(4) 0.2489(6) 0.7807(4) 0.0751(16) Uani 1 1 d . . .
H21 H 0.8647 0.2189 0.7674 0.090 Uiso 1 1 calc R . .
C22 C 0.7799(4) 0.1960(5) 0.8514(4) 0.0707(15) Uani 1 1 d . . .
H22 H 0.8184 0.1294 0.8868 0.085 Uiso 1 1 calc R . .
C23 C 0.4760(3) 0.4783(4) 0.7796(3) 0.0452(10) Uani 1 1 d . . .
C24 C 0.7137(5) 0.0708(5) 1.0070(3) 0.081(2) Uani 1 1 d . . .
O5 O 1.0000 0.0000 1.0000 0.144(3) Uani 1 2 d S . .
H1W H 1.0412 -0.0580 1.0024 0.217 Uiso 0.50 1 d PR . .
H2W H 0.9689 0.0241 1.0381 0.217 Uiso 0.50 1 d PR . .
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'
Zn Zn 0.2839 1.4301 '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
O3 Zn1 O1 104.94(17) 4_565 .
O3 Zn1 N1 117.76(14) 4_565 .
O1 Zn1 N1 124.76(14) . .
O3 Zn1 N2 97.06(13) 4_565 4_576
O1 Zn1 N2 100.20(13) . 4_576
N1 Zn1 N2 107.11(11) . 4_576
C5 N1 C1 117.4(3) . .
C5 N1 Zn1 120.6(2) . .
C1 N1 Zn1 121.1(2) . .
C11 N2 C10 117.2(3) . .
C11 N2 Zn1 123.4(2) . 4_675
C10 N2 Zn1 118.9(2) . 4_675
C23 O1 Zn1 110.2(3) . .
C24 O3 Zn1 126.5(3) . 4_666
N1 C1 C2 122.4(3) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 119.1(3) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 119.6(3) . .
C2 C3 H3 120.2 . .
C4 C3 H3 120.2 . .
C3 C4 C5 117.3(3) . .
C3 C4 C6 124.3(3) . .
C5 C4 C6 118.4(3) . .
N1 C5 C4 124.1(3) . .
N1 C5 H5 118.0 . .
C4 C5 H5 118.0 . .
C7 C6 C4 126.1(4) . .
C7 C6 H6 116.9 . .
C4 C6 H6 116.9 . .
C6 C7 C8 126.2(4) . .
C6 C7 H7 116.9 . .
C8 C7 H7 116.9 . .
C12 C8 C9 116.3(3) . .
C12 C8 C7 123.9(3) . .
C9 C8 C7 119.8(3) . .
C10 C9 C8 120.4(3) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
N2 C10 C9 122.6(3) . .
N2 C10 H10 118.7 . .
C9 C10 H10 118.7 . .
N2 C11 C12 123.2(3) . .
N2 C11 H11 118.4 . .
C12 C11 H11 118.4 . .
C11 C12 C8 120.3(3) . .
C11 C12 H12 119.8 . .
C8 C12 H12 119.8 . .
C14 C13 C18 119.8(3) . .
C14 C13 C23 116.9(4) . .
C18 C13 C23 123.2(4) . .
C13 C14 C15 121.2(4) . .
C13 C14 H14 119.4 . .
C15 C14 H14 119.4 . .
C16 C15 C14 121.3(4) . .
C16 C15 H15 119.3 . .
C14 C15 H15 119.3 . .
C15 C16 C17 119.5(4) . .
C15 C16 C24 117.5(4) . .
C17 C16 C24 123.0(4) . .
C22 C17 C16 122.8(4) . .
C22 C17 C18 117.9(4) . .
C16 C17 C18 119.3(4) . .
C19 C18 C13 124.1(3) . .
C19 C18 C17 117.4(4) . .
C13 C18 C17 118.5(4) . .
C20 C19 C18 122.4(4) . .
C20 C19 H19 118.8 . .
C18 C19 H19 118.8 . .
C19 C20 C21 119.5(5) . .
C19 C20 H20 120.2 . .
C21 C20 H20 120.2 . .
C22 C21 C20 121.2(5) . .
C22 C21 H21 119.4 . .
C20 C21 H21 119.4 . .
C21 C22 C17 121.7(5) . .
C21 C22 H22 119.2 . .
C17 C22 H22 119.2 . .
O1 C23 O2' 112.2(7) . .
O1 C23 O2 117.3(4) . .
O2' C23 O2 54.8(9) . .
O1 C23 C13 118.6(4) . .
O2' C23 C13 117.7(6) . .
O2 C23 C13 119.8(4) . .
O3 C24 O4 117.0(6) . .
O3 C24 O4' 101.8(7) . .
O4 C24 O4' 76.9(8) . .
O3 C24 C16 119.1(4) . .
O4 C24 C16 118.2(5) . .
O4' C24 C16 113.7(6) . .
H1W O5 H2W 134.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O3 1.931(3) 4_565
Zn1 O1 1.968(3) .
Zn1 N1 2.029(3) .
Zn1 N2 2.074(3) 4_576
N1 C5 1.332(4) .
N1 C1 1.340(4) .
N2 C11 1.337(4) .
N2 C10 1.343(5) .
N2 Zn1 2.074(3) 4_675
O1 C23 1.214(5) .
O2 C23 1.287(7) .
O2' C23 1.287(12) .
O3 C24 1.166(5) .
O3 Zn1 1.931(3) 4_666
O4 C24 1.215(8) .
O4' C24 1.487(12) .
C1 C2 1.377(5) .
C1 H1 0.9400 .
C2 C3 1.374(5) .
C2 H2 0.9400 .
C3 C4 1.376(5) .
C3 H3 0.9400 .
C4 C5 1.384(5) .
C4 C6 1.470(5) .
C5 H5 0.9400 .
C6 C7 1.319(5) .
C6 H6 0.9400 .
C7 C8 1.452(5) .
C7 H7 0.9400 .
C8 C12 1.387(5) .
C8 C9 1.388(5) .
C9 C10 1.374(5) .
C9 H9 0.9400 .
C10 H10 0.9400 .
C11 C12 1.365(5) .
C11 H11 0.9400 .
C12 H12 0.9400 .
C13 C14 1.360(5) .
C13 C18 1.428(5) .
C13 C23 1.509(5) .
C14 C15 1.411(5) .
C14 H14 0.9400 .
C15 C16 1.359(6) .
C15 H15 0.9400 .
C16 C17 1.426(6) .
C16 C24 1.513(6) .
C17 C22 1.425(7) .
C17 C18 1.444(5) .
C18 C19 1.413(6) .
C19 C20 1.359(6) .
C19 H19 0.9400 .
C20 C21 1.398(8) .
C20 H20 0.9400 .
C21 C22 1.336(8) .
C21 H21 0.9400 .
C22 H22 0.9400 .
O5 H1W 0.8500 .
O5 H2W 0.8499 .
