#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:54:20 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258151 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558617.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_1558617
loop_
_publ_author_name
'Ling, Xia'
'Huang, Letao'
'Li, Youzhen'
'Wan, Qing'
'Wang, Zhiming'
'Qin, Anjun'
'Gao, Meng'
'Tang, Ben Zhong'
_publ_section_title
;
 Photoactivatable dihydroalkaloids for cancer cell imaging and
 chemotherapy with high spatiotemporal resolution
;
_journal_issue                   10
_journal_name_full               'Materials Horizons'
_journal_page_first              2696
_journal_page_last               2701
_journal_paper_doi               10.1039/D0MH00931H
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         'Cl, C21 H18 N O4, C H4 O'
_chemical_formula_sum            'C22 H22 Cl N O5'
_chemical_formula_weight         415.85
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-15 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.917(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.288(6)
_cell_length_b                   8.182(3)
_cell_length_c                   17.804(7)
_cell_measurement_reflns_used    7032
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.75
_cell_volume                     1921.6(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17063
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_min         2.615
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0701 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045
_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     267
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0357
_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/[σ²(Fo²)+(0.0462P)²+0.7795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3545
_reflns_number_total             4215
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0mh00931h3.cif
_cod_data_source_block           191012_che_0m
_cod_depositor_comments
'Adding full bibliography for 1558616--1558618.cif.'
_cod_original_cell_volume        1921.7(14)
_cod_database_code               1558617
_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.
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C14(H14), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl1 Cl 0.65404(3) 0.01266(5) 0.30490(2) 0.03013(11) Uani 1 1 d . . . . .
O1 O 0.13867(9) -0.08002(15) 0.33923(6) 0.0350(3) Uani 1 1 d . . . . .
O2 O 0.27038(8) 0.08829(14) 0.26108(6) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.88599(8) 0.59433(16) 0.46582(6) 0.0370(3) Uani 1 1 d . . . . .
O4 O 0.89343(9) 0.62710(16) 0.59536(6) 0.0373(3) Uani 1 1 d . . . . .
N1 N 0.51878(9) 0.32110(15) 0.36972(6) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.32536(11) 0.06075(19) 0.49669(8) 0.0263(3) Uani 1 1 d . . . . .
H1 H 0.337285 0.054634 0.550308 0.032 Uiso 1 1 calc R . . . .
C2 C 0.24134(12) -0.01383(19) 0.45900(9) 0.0278(3) Uani 1 1 d . . . . .
H2 H 0.196676 -0.071953 0.487215 0.033 Uiso 1 1 calc R . . . .
C3 C 0.21971(11) -0.00640(18) 0.37972(9) 0.0259(3) Uani 1 1 d . . . . .
C4 C 0.28471(11) 0.07848(18) 0.33852(8) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.37223(11) 0.15365(17) 0.37693(8) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.39389(11) 0.14603(17) 0.45675(8) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.48330(11) 0.22798(18) 0.49197(8) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.54958(11) 0.31115(17) 0.44856(7) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.43680(11) 0.24588(18) 0.33705(8) 0.0224(3) Uani 1 1 d . . . . .
H9 H 0.420991 0.254982 0.283737 0.027 Uiso 1 1 calc R . . . .
C10 C 0.50450(11) 0.22816(18) 0.57245(8) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.462036 0.168146 0.601750 0.030 Uiso 1 1 calc R . . . .
C11 C 0.58406(12) 0.31239(19) 0.60764(8) 0.0259(3) Uani 1 1 d . . . . .
H11 H 0.593716 0.316941 0.661338 0.031 Uiso 1 1 calc R . . . .
C12 C 0.65342(11) 0.39409(18) 0.56604(8) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.64195(11) 0.38613(18) 0.48489(8) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.72364(11) 0.4488(2) 0.44770(8) 0.0275(3) Uani 1 1 d . . . . .
H14 H 0.724224 0.435190 0.394766 0.033 Uiso 1 1 calc R . . . .
C15 C 0.80036(11) 0.5282(2) 0.49030(9) 0.0282(3) Uani 1 1 d . . . . .
C16 C 0.80594(12) 0.5459(2) 0.56860(9) 0.0283(3) Uani 1 1 d . . . . .
C17 C 0.73630(12) 0.47692(19) 0.60812(8) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.742319 0.483301 0.661749 0.033 Uiso 1 1 calc R . . . .
C18 C 0.93408(13) 0.6853(2) 0.52915(10) 0.0360(4) Uani 1 1 d . . . . .
H18A H 0.920076 0.803467 0.521982 0.043 Uiso 1 1 calc R . . . .
H18B H 1.008371 0.668472 0.534371 0.043 Uiso 1 1 calc R . . . .
C19 C 0.06612(13) -0.1602(2) 0.37964(10) 0.0380(4) Uani 1 1 d . . . . .
H19A H 0.013827 -0.211054 0.343608 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.034634 -0.080012 0.410402 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.100176 -0.244405 0.412616 0.057 Uiso 1 1 calc GR . . . .
C20 C 0.17882(13) 0.1702(2) 0.22890(9) 0.0349(4) Uani 1 1 d . . . . .
H20A H 0.187953 0.212062 0.178592 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.164297 0.261304 0.261671 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.122148 0.092790 0.224615 0.052 Uiso 1 1 calc GR . . . .
C21 C 0.57269(12) 0.4198(2) 0.31706(8) 0.0271(3) Uani 1 1 d . . . . .
H21A H 0.632283 0.359619 0.304660 0.041 Uiso 1 1 calc GR . . . .
H21B H 0.594252 0.523773 0.341170 0.041 Uiso 1 1 calc GR . . . .
H21C H 0.527116 0.441123 0.270620 0.041 Uiso 1 1 calc GR . . . .
O5 O 0.86806(10) 0.1149(2) 0.38053(7) 0.0508(4) Uani 1 1 d . . . . .
H5 H 0.809347 0.076040 0.371311 0.076 Uiso 1 1 calc GR . . . .
C22 C 0.89855(17) 0.1795(3) 0.31386(12) 0.0618(6) Uani 1 1 d . . . . .
H22A H 0.899014 0.092481 0.276075 0.093 Uiso 1 1 calc GR . . . .
H22B H 0.966798 0.225679 0.324713 0.093 Uiso 1 1 calc GR . . . .
H22C H 0.851148 0.265426 0.294237 0.093 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 '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
C3 O1 C19 118.33(13) . . ?
C4 O2 C20 115.72(11) . . ?
C15 O3 C18 105.17(12) . . ?
C16 O4 C18 105.18(12) . . ?
C8 N1 C21 123.57(12) . . ?
C9 N1 C8 122.23(12) . . ?
C9 N1 C21 114.17(12) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.72(14) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.75(14) . . ?
C3 C2 H2 119.1 . . ?
O1 C3 C2 124.37(14) . . ?
O1 C3 C4 116.43(13) . . ?
C4 C3 C2 119.19(14) . . ?
O2 C4 C3 122.81(14) . . ?
O2 C4 C5 117.81(13) . . ?
C3 C4 C5 119.34(13) . . ?
C4 C5 C6 121.39(13) . . ?
C9 C5 C4 120.48(13) . . ?
C9 C5 C6 118.03(13) . . ?
C1 C6 C5 117.60(13) . . ?
C1 C6 C7 124.14(13) . . ?
C5 C6 C7 118.25(13) . . ?
C8 C7 C6 121.43(12) . . ?
C8 C7 C10 119.19(13) . . ?
C10 C7 C6 119.37(13) . . ?
N1 C8 C13 123.02(12) . . ?
C7 C8 N1 116.39(13) . . ?
C7 C8 C13 120.55(12) . . ?
N1 C9 C5 123.40(13) . . ?
N1 C9 H9 118.3 . . ?
C5 C9 H9 118.3 . . ?
C7 C10 H10 119.5 . . ?
C11 C10 C7 121.00(14) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.33(13) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 120.49(14) . . ?
C11 C12 C17 117.33(13) . . ?
C17 C12 C13 122.12(14) . . ?
C12 C13 C8 116.67(13) . . ?
C14 C13 C8 126.30(13) . . ?
C14 C13 C12 117.01(13) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.16(14) . . ?
C15 C14 H14 120.9 . . ?
O3 C15 C16 109.21(14) . . ?
C14 C15 O3 127.11(14) . . ?
C14 C15 C16 123.58(15) . . ?
O4 C16 C15 109.76(14) . . ?
C17 C16 O4 128.71(14) . . ?
C17 C16 C15 121.29(15) . . ?
C12 C17 H17 121.3 . . ?
C16 C17 C12 117.31(14) . . ?
C16 C17 H17 121.3 . . ?
O3 C18 O4 107.29(13) . . ?
O3 C18 H18A 110.3 . . ?
O3 C18 H18B 110.3 . . ?
O4 C18 H18A 110.3 . . ?
O4 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O5 H5 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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 C3 1.3621(19) . ?
O1 C19 1.430(2) . ?
O2 C4 1.3712(18) . ?
O2 C20 1.4457(19) . ?
O3 C15 1.3774(19) . ?
O3 C18 1.435(2) . ?
O4 C16 1.3734(19) . ?
O4 C18 1.436(2) . ?
N1 C8 1.4163(18) . ?
N1 C9 1.3233(19) . ?
N1 C21 1.4854(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(2) . ?
C1 C6 1.406(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.408(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.417(2) . ?
C5 C9 1.399(2) . ?
C6 C7 1.441(2) . ?
C7 C8 1.414(2) . ?
C7 C10 1.427(2) . ?
C8 C13 1.453(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.351(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.418(2) . ?
C12 C13 1.436(2) . ?
C12 C17 1.426(2) . ?
C13 C14 1.433(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.360(2) . ?
C15 C16 1.395(2) . ?
C16 C17 1.352(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O5 H5 0.8400 . ?
O5 C22 1.403(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
