Research on single-crystal-to-single-crystal photoaddition and extension of Schmidt's rule in topological chemistry
Xiao, Cheng-Yue; Deng, Xi-Ling; Wei, Zan-Bin; Yang, Shi-Yao; CrystEngComm 25 (2023) 3714–3717; doi:10.1039/D3CE00443K

data_7246938
_publ_section_title
;
 Research on single-crystal-to-single-crystal photoaddition and extension
 of Schmidt's rule in topological chemistry
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              3714
_journal_page_last               3717
_journal_paper_doi               10.1039/D3CE00443K
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C29 H20 N2 O7 Zn2, H7.7 O3.85'
_chemical_formula_sum            'C29 H27.7 N2 O10.85 Zn2'
_chemical_formula_weight         708.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-24 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                78.835(9)
_cell_angle_beta                 84.141(9)
_cell_angle_gamma                69.710(11)
_cell_formula_units_Z            2
_cell_length_a                   8.7170(10)
_cell_length_b                   9.9589(12)
_cell_length_c                   19.6815(14)
_cell_measurement_reflns_used    4330
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.40236
_cell_volume                     1571.1(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10747
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.026
_diffrn_reflns_theta_min         4.583
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  0.7954
_exptl_absorpt_correction_T_min  0.5853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             725
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.325
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         6160
_refine_ls_number_restraints     552
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0890
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2524
_refine_ls_wR_factor_ref         0.3068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4344
_reflns_number_total             6160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00443k2.cif
_cod_data_source_block           363
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7246935--7246938.cif.
;
_cod_original_formula_sum        'C29 H27.70 N2 O10.85 Zn2'
_cod_database_code               7246938
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.585
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-H7
 0.85 with sigma of 0.01
 O1W-H1WA = O1W-H1WB = O2W-H2WA = O2W-H2WB = O3W-H3WA = O3W-H3WB
 0.85 with sigma of 0.01
 H1WA-H1WB = H2WA-H2WB = H3WA-H3WB
 1.38 with sigma of 0.01
 O4W-H4WA = O4W-H4WB = O5W-H5WA = O5W-H5WB = O6W-H6W = O6W-H2WC
 0.85 with sigma of 0.01
 H4WA-H4WB = H5WA-H5WB = H6W-H2WC
 1.38 with sigma of 0.01
 O7W-H2W = O7W-H1W = O8W-H8WA = O8W-H8WB = O9W-H8WC = O9W-H8WD
 0.85 with sigma of 0.01
 H2W-H1W = H8WA-H8WB = H8WC-H8WD
 1.38 with sigma of 0.01
 O10W-H6WA = O10W-H10W = O11W-H11W = O11W-H5W = O12W-H4WC = O12W-H4WD
 0.85 with sigma of 0.01
 H6WA-H10W = H11W-H5W = H4WC-H4WD
 1.38 with sigma of 0.01
 O13W-H13W = O13W-H3W = O14W-H3WC = O14W-H14W = O15W-H15A = O15W-H15B
 0.85 with sigma of 0.01
 H13W-H3W = H3WC-H14W = H15A-H15B
 1.38 with sigma of 0.01
 O16W-H16A = O16W-H16B
 0.85 with sigma of 0.01
 H16A-H16B
 1.38 with sigma of 0.01
 C12'-C15' = C16'-C17' = C20'-C23' = C24'-C25'
 1.49 with sigma of 0.01
 C121-C151 = C161-C171 = C201-C231 = C241-C251
 1.49 with sigma of 0.01
 C18-C19
 1.38 with sigma of 0.01
 C15'-C16' = C151-C161 = C23'-C24' = C231-C241
 1.55 with sigma of 0.01
 C15'-C24'_$1 = C16'-C23'_$1
 1.57 with sigma of 0.01
 C151-C241_$1 = C161-C231_$1
 1.57 with sigma of 0.01
 C24'-C26' \\sim C24'-C28'
 with sigma of 0.01
3. Restrained planarity
 C171, C181, C191, C201, C211, C221
 with sigma of 0.01
 N1, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24,
  C25, C26, C27, C28, C29, N2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N1 \\sim N1' \\sim N11: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C10 \\sim C10' \\sim C101: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C11 \\sim C11' \\sim C111: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C12 \\sim C12' \\sim C121: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C13 \\sim C13' \\sim C131: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C14 \\sim C14' \\sim C141: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C15 \\sim C15' \\sim C151 \\sim C16 \\sim C16' \\sim C161 \\sim C23 \\sim C23'
\\sim C231 \\sim C24 \\sim C24' \\sim C241: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
C17 \\sim C17' \\sim C171: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C18 \\sim C18' \\sim C181: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C19 \\sim C19' \\sim C191: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C20 \\sim C20' \\sim C201: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C21 \\sim C21' \\sim C211: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C22 \\sim C22' \\sim C221: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C23 \\sim C23' \\sim C231: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C24 \\sim C24' \\sim C241: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C25 \\sim C25' \\sim C251: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C26 \\sim C26' \\sim C261: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C27 \\sim C27' \\sim C271: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C28 \\sim C28' \\sim C281: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
C29 \\sim C29' \\sim C291: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
N2 \\sim N2' \\sim N21: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
5. Same fragment restrains
{N1, C10, C11, C12, C13, C14} sigma for 1-2: 0.02, 1-3: 0.04
as in
{N1', C10', C11', C12', C13', C14'}
{C17, C18, C19, C20, C21, C22} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C171, C181, C191, C201, C211, C221}
{C25, C26, C27, C28, C29, N2} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C251, C261, C271, C281, C291, N21}
{C17, C18, C19, C20, C21, C22} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C17', C18', C19', C20', C21', C22'}
{C25, C26, C27, C28, C29, N2} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C25', C26', C27', C28', C29', N2'}
{N1, C10, C11, C12, C13, C14} sigma for 1-2: 0.02, 1-3: 0.04
as in
{N11, C101, C111, C121, C131, C141}
6. Others
 1*[Sof(N1)+Sof(C10)+Sof(H10)+Sof(C11)+Sof(H11)+Sof(C12)+Sof(C13)+Sof(H13)+
 Sof(C14)+Sof(H14)+Sof(C15)+Sof(H15)+Sof(C16)+Sof(H16)+Sof(C17)+Sof(C18)+
 Sof(H18)+Sof(C19)+Sof(H19)+Sof(C20)+Sof(C21)+Sof(H21)+Sof(C22)+Sof(H22)+
 Sof(C23)+Sof(H23)+Sof(C24)+Sof(H24)+Sof(C25)+Sof(C26)+Sof(H26)+Sof(C27)+
 Sof(H27)+Sof(C28)+Sof(H28)+Sof(C29)+Sof(H29)+Sof(N2)]+1*[Sof(N1')+Sof(C10')+
 Sof(H10')+Sof(C11')+Sof(H11')+Sof(C12')+Sof(C13')+Sof(H13')+Sof(C14')+
 Sof(H14')+Sof(C15')+Sof(H15')+Sof(C16')+Sof(H16')+Sof(C17')+Sof(C18')+
 Sof(H18')+Sof(C19')+Sof(H19')+Sof(C20')+Sof(C21')+Sof(H21')+Sof(C22')+
 Sof(H22')+Sof(C23')+Sof(H23')+Sof(C24')+Sof(H24')+Sof(C25')+Sof(C26')+
 Sof(H26')+Sof(C27')+Sof(H27')+Sof(C28')+Sof(H28')+Sof(C29')+Sof(H29')+
 Sof(N2')]+1*[Sof(N11)+Sof(C101)+Sof(H101)+Sof(C111)+Sof(H111)+Sof(C121)+
 Sof(C131)+Sof(H131)+Sof(C141)+Sof(H141)+Sof(C151)+Sof(H151)+Sof(C161)+
 Sof(H161)+Sof(C171)+Sof(C181)+Sof(H181)+Sof(C191)+Sof(H191)+Sof(C201)+
 Sof(C211)+Sof(H211)+Sof(C221)+Sof(H221)+Sof(C231)+Sof(H231)+Sof(C241)+
 Sof(H241)+Sof(C251)+Sof(C261)+Sof(H261)+Sof(C271)+Sof(H271)+Sof(C281)+
 Sof(H281)+Sof(C291)+Sof(H291)+Sof(N21)]=1 with esd of 0.0001
 Sof(N1)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=
 Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=
 Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(N2)=FVAR(1)
 Sof(N1')=Sof(C10')=Sof(H10')=Sof(C11')=Sof(H11')=Sof(C12')=Sof(C13')=
 Sof(H13')=Sof(C14')=Sof(H14')=Sof(C15')=Sof(H15')=Sof(C16')=Sof(H16')=
 Sof(C17')=Sof(C18')=Sof(H18')=Sof(C19')=Sof(H19')=Sof(C20')=Sof(C21')=
 Sof(H21')=Sof(C22')=Sof(H22')=Sof(C23')=Sof(H23')=Sof(C24')=Sof(H24')=
 Sof(C25')=Sof(C26')=Sof(H26')=Sof(C27')=Sof(H27')=Sof(C28')=Sof(H28')=
 Sof(C29')=Sof(H29')=Sof(N2')=FVAR(2)
 Sof(N11)=Sof(C101)=Sof(H101)=Sof(C111)=Sof(H111)=Sof(C121)=Sof(C131)=
 Sof(H131)=Sof(C141)=Sof(H141)=Sof(C151)=Sof(H151)=Sof(C161)=Sof(H161)=
 Sof(C171)=Sof(C181)=Sof(H181)=Sof(C191)=Sof(H191)=Sof(C201)=Sof(C211)=
 Sof(H211)=Sof(C221)=Sof(H221)=Sof(C231)=Sof(H231)=Sof(C241)=Sof(H241)=
 Sof(C251)=Sof(C261)=Sof(H261)=Sof(C271)=Sof(H271)=Sof(C281)=Sof(H281)=
 Sof(C291)=Sof(H291)=Sof(N21)=FVAR(3)
 Fixed Sof: O1W(0.3) H1WA(0.3) H1WB(0.3) O2W(0.3) H2WA(0.3) H2WB(0.3)
 O3W(0.25) H3WA(0.25) H3WB(0.25) O4W(0.2) H4WA(0.2) H4WB(0.2) O5W(0.25)
 H5WA(0.25) H5WB(0.25) O6W(0.25) H6W(0.25) H2WC(0.25) O7W(0.3) H2W(0.3)
 H1W(0.3) O8W(0.3) H8WA(0.3) H8WB(0.3) O9W(0.2) H8WC(0.2) H8WD(0.2) O10W(0.25)
 H6WA(0.25) H10W(0.25) O11W(0.2) H11W(0.2) H5W(0.2) O12W(0.2) H4WC(0.2)
 H4WD(0.2) O13W(0.25) H13W(0.25) H3W(0.25) O14W(0.2) H3WC(0.2) H14W(0.2)
 O15W(0.2) H15A(0.2) H15B(0.2) O16W(0.2) H16A(0.2) H16B(0.2)
7.a Ternary CH refined with riding coordinates:
 C15'(H15'), C16'(H16'), C23'(H23'), C24'(H24'), C151(H151), C161(H161),
 C231(H231), C241(H241)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C10'(H10'), C11'(H11'), C13'(H13'), C14'(H14'),
 C18'(H18'), C19'(H19'), C21'(H21'), C22'(H22'), C26'(H26'), C27'(H27'),
 C28'(H28'), C29'(H29'), C101(H101), C111(H111), C131(H131), C141(H141),
 C181(H181), C191(H191), C211(H211), C221(H221), C261(H261), C271(H271),
 C281(H281), C291(H291)
;
_shelx_res_checksum              96430
_shelx_hkl_checksum              10982
_olex2_submission_special_instructions 'No special instructions were received'