#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/35/7123578.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_7123578
loop_
_publ_author_name
'Zhu, Shifa'
'Zhang, Jiantao'
'Liao, Zhehui'
'Chen, Lianfen'
'Jiang, Huanfeng'
_publ_section_title
;
 Construction of polycyclic bridged indene derivatives by a tandem
 1,3-rearrangement/intramolecular Friedel-Crafts cyclization of propargyl
 acetates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03715B
_journal_year                    2019
_chemical_formula_moiety         'C25 H23 Cl O5'
_chemical_formula_sum            'C25 H23 Cl O5'
_chemical_formula_weight         438.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-08 deposited with the CCDC.    2019-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                69.694(11)
_cell_angle_beta                 76.371(11)
_cell_angle_gamma                62.034(13)
_cell_formula_units_Z            2
_cell_length_a                   10.7102(14)
_cell_length_b                   11.1405(13)
_cell_length_c                   11.3689(13)
_cell_measurement_reflns_used    2995
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9250
_cell_measurement_theta_min      4.1530
_cell_volume                     1119.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  49.00   1.00    1.00    --   40.23  38.00  60.00   33
  2  ω     83.00 163.00   1.00    1.00    --  108.20  45.00 -30.00   80
  3  ω    105.00 175.00   1.00    1.00    --  108.20 129.00   5.00   70
  4  ω     95.00 160.00   1.00    1.00    --  108.20 125.00 -30.00   65
  5  ω     87.00 162.00   1.00    1.00    --  108.20  30.00  30.00   75
  6  ω     85.00 177.00   1.00    1.00    --  108.20  61.00  60.00   92
  7  ω     83.00 110.00   1.00    1.00    --  108.20 -45.00  30.00   27
  8  ω     67.00 109.00   1.00    1.00    --  108.20 -95.00 -60.00   42
  9  ω     66.00 140.00   1.00    1.00    --  108.20 -77.00   0.00   74
 10  ω     52.00  84.00   1.00    1.00    --   40.23-125.00 -30.00   32
 11  ω     37.00 119.00   1.00    1.00    --  108.20-125.00-150.00   82
 12  ω     39.00 137.00   1.00    1.00    --  108.20 -61.00 -90.00   98
 13  ω     57.00 107.00   1.00    1.00    --  108.20  15.00-180.00   50
 14  ω     53.00  80.00   1.00    1.00    --  108.20 -45.00  30.00   27
 15  ω     51.00  80.00   1.00    1.00    --   40.23 -99.00 150.00   29
 16  ω    -29.00  63.00   1.00    1.00    --   40.23 -38.00-120.00   92
 17  ω    -67.00  33.00   1.00    1.00    --  -40.23  57.00-180.00  100
 18  ω   -114.00 -20.00   1.00    1.00    --  -40.23 -77.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0417767000
_diffrn_orient_matrix_UB_12      -0.1182854000
_diffrn_orient_matrix_UB_13      0.1237666000
_diffrn_orient_matrix_UB_21      0.0849376000
_diffrn_orient_matrix_UB_22      -0.1097543000
_diffrn_orient_matrix_UB_23      -0.0753656000
_diffrn_orient_matrix_UB_31      0.1333049000
_diffrn_orient_matrix_UB_32      0.0221457000
_diffrn_orient_matrix_UB_33      -0.0064219000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7321
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.435
_diffrn_reflns_theta_min         4.162
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0971
_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)+(0.1789P)²+2.2617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2885
_refine_ls_wR_factor_ref         0.3048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3577
_reflns_number_total             4371
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03715b2.cif
_cod_data_source_block           zft_2
_cod_database_code               7123578
_shelx_shelxl_version_number     2018/3
_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   0.841
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C5(H5), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C21(H21), C11(H11), C14(H14), C20(H20), C13(H13), C19(H19),
 C12(H12), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2018-12-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.867
_oxdiff_exptl_absorpt_empirical_full_min 0.553
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl 1.01655(11) 0.14488(12) 0.10943(10) 0.0354(4) Uani 1 1 d .
O1 O 0.6104(3) 0.4064(3) 0.3960(3) 0.0278(7) Uani 1 1 d .
O3 O 0.7265(3) 0.5770(3) 0.4526(3) 0.0335(7) Uani 1 1 d .
O5 O 0.8276(3) 0.3286(4) 0.6903(3) 0.0342(7) Uani 1 1 d .
O4 O 1.0289(3) 0.1776(4) 0.6114(3) 0.0371(8) Uani 1 1 d .
O2 O 0.9282(4) 0.4907(4) 0.3344(4) 0.0450(9) Uani 1 1 d .
C15 C 0.4630(5) 0.3565(5) 0.2307(4) 0.0294(9) Uani 1 1 d .
H15 H 0.407156 0.392977 0.297118 0.035 Uiso 1 1 calc R
C21 C 0.2446(4) 0.3852(5) 0.1666(4) 0.0299(9) Uani 1 1 d .
H21 H 0.202547 0.393509 0.246625 0.036 Uiso 1 1 calc R
C9 C 0.6703(5) 0.2078(5) 0.5655(4) 0.0293(9) Uani 1 1 d .
C8 C 0.6751(4) 0.3489(5) 0.5137(4) 0.0265(9) Uani 1 1 d .
H8 H 0.623172 0.409075 0.570686 0.032 Uiso 1 1 calc R
C7 C 0.8334(4) 0.3293(4) 0.4799(4) 0.0264(9) Uani 1 1 d .
C11 C 0.6615(4) 0.0424(5) 0.4781(4) 0.0318(9) Uani 1 1 d .
H11 H 0.659907 0.016148 0.409432 0.038 Uiso 1 1 calc R
C10 C 0.6661(4) 0.1683(5) 0.4625(4) 0.0286(9) Uani 1 1 d .
C24 C 0.9100(4) 0.2685(5) 0.5998(4) 0.0280(9) Uani 1 1 d .
C16 C 0.3857(5) 0.3675(5) 0.1346(4) 0.0292(9) Uani 1 1 d .
C22 C 0.8366(5) 0.4732(5) 0.4130(4) 0.0282(9) Uani 1 1 d .
C14 C 0.6715(5) 0.1197(5) 0.6866(4) 0.0346(10) Uani 1 1 d .
H14 H 0.676637 0.144457 0.754876 0.042 Uiso 1 1 calc R
C4 C 0.6712(4) 0.2869(5) 0.3461(4) 0.0278(9) Uani 1 1 d .
C20 C 0.1661(5) 0.3905(5) 0.0823(4) 0.0340(10) Uani 1 1 d .
H20 H 0.073462 0.400162 0.106757 0.041 Uiso 1 1 calc R
C5 C 0.8237(4) 0.2658(5) 0.2927(4) 0.0285(9) Uani 1 1 d .
H5 H 0.819349 0.355717 0.233814 0.034 Uiso 1 1 calc R
C6 C 0.9154(4) 0.2265(5) 0.3960(4) 0.0287(9) Uani 1 1 d .
H6A H 1.004012 0.233401 0.358791 0.034 Uiso 1 1 calc R
H6B H 0.937230 0.129988 0.446582 0.034 Uiso 1 1 calc R
C25 C 0.8937(5) 0.2738(5) 0.8073(4) 0.0377(11) Uani 1 1 d .
H25A H 0.976011 0.292136 0.792228 0.057 Uiso 1 1 calc GR
H25B H 0.921312 0.173753 0.838227 0.057 Uiso 1 1 calc GR
H25C H 0.827371 0.319414 0.868528 0.057 Uiso 1 1 calc GR
C3 C 0.6034(5) 0.3010(5) 0.2361(4) 0.0287(9) Uani 1 1 d .
C2 C 0.7238(5) 0.2346(6) 0.1449(4) 0.0358(10) Uani 1 1 d .
H2A H 0.730738 0.305855 0.068208 0.043 Uiso 1 1 calc R
H2B H 0.709933 0.164827 0.123531 0.043 Uiso 1 1 calc R
C1 C 0.8583(4) 0.1641(5) 0.2157(4) 0.0302(9) Uani 1 1 d .
H1 H 0.867811 0.071469 0.272222 0.036 Uiso 1 1 calc R
C13 C 0.6647(6) -0.0060(5) 0.7032(5) 0.0404(11) Uani 1 1 d .
H13 H 0.663844 -0.065875 0.784012 0.049 Uiso 1 1 calc R
C19 C 0.2252(5) 0.3816(5) -0.0377(5) 0.0380(11) Uani 1 1 d .
H19 H 0.173020 0.384325 -0.094227 0.046 Uiso 1 1 calc R
C12 C 0.6592(5) -0.0450(5) 0.6009(5) 0.0369(10) Uani 1 1 d .
H12 H 0.653914 -0.129812 0.614455 0.044 Uiso 1 1 calc R
C17 C 0.4429(5) 0.3617(6) 0.0111(4) 0.0365(10) Uani 1 1 d .
H17 H 0.535066 0.353359 -0.014625 0.044 Uiso 1 1 calc R
C23 C 0.7168(5) 0.7173(5) 0.3920(5) 0.0401(11) Uani 1 1 d .
H23A H 0.725608 0.734350 0.302350 0.060 Uiso 1 1 calc GR
H23B H 0.791655 0.726538 0.415545 0.060 Uiso 1 1 calc GR
H23C H 0.626708 0.784901 0.417707 0.060 Uiso 1 1 calc GR
C18 C 0.3625(6) 0.3685(6) -0.0733(5) 0.0410(11) Uani 1 1 d .
H18 H 0.401961 0.364217 -0.154730 0.049 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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 O1 C8 102.8(3)
C22 O3 C23 116.4(4)
C24 O5 C25 114.2(4)
C3 C15 C16 128.7(4)
C20 C21 C16 121.8(4)
C10 C9 C8 106.7(4)
C14 C9 C8 132.5(4)
C14 C9 C10 120.7(4)
O1 C8 C9 102.9(3)
O1 C8 C7 107.2(3)
C9 C8 C7 110.1(3)
C24 C7 C8 110.6(3)
C24 C7 C6 108.2(3)
C22 C7 C8 109.6(3)
C22 C7 C24 107.0(3)
C22 C7 C6 110.5(3)
C6 C7 C8 110.9(3)
C10 C11 C12 117.8(4)
C9 C10 C4 106.1(4)
C11 C10 C9 121.4(4)
C11 C10 C4 132.5(4)
O5 C24 C7 111.6(4)
O4 C24 O5 124.0(4)
O4 C24 C7 124.4(4)
C21 C16 C15 118.3(4)
C21 C16 C17 117.2(4)
C17 C16 C15 124.4(4)
O3 C22 C7 112.0(4)
O2 C22 O3 123.7(4)
O2 C22 C7 124.2(4)
C13 C14 C9 118.2(4)
O1 C4 C10 102.2(3)
O1 C4 C5 107.0(3)
O1 C4 C3 116.8(3)
C10 C4 C5 112.6(3)
C3 C4 C10 114.1(4)
C3 C4 C5 104.2(3)
C19 C20 C21 120.2(4)
C6 C5 C4 111.5(3)
C6 C5 C1 121.0(4)
C1 C5 C4 100.2(3)
C5 C6 C7 108.8(3)
C15 C3 C4 123.7(4)
C15 C3 C2 129.7(4)
C2 C3 C4 106.5(3)
C3 C2 C1 104.8(3)
C5 C1 Cl1 113.0(3)
C5 C1 C2 102.0(3)
C2 C1 Cl1 112.1(3)
C14 C13 C12 121.2(5)
C20 C19 C18 119.4(4)
C13 C12 C11 120.7(5)
C18 C17 C16 120.5(4)
C19 C18 C17 121.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.804(4)
O1 C8 1.451(5)
O1 C4 1.434(5)
O3 C22 1.328(5)
O3 C23 1.436(6)
O5 C24 1.335(5)
O5 C25 1.455(5)
O4 C24 1.200(5)
O2 C22 1.201(6)
C15 C16 1.461(6)
C15 C3 1.339(6)
C21 C16 1.402(6)
C21 C20 1.386(6)
C9 C8 1.497(6)
C9 C10 1.403(6)
C9 C14 1.385(7)
C8 C7 1.572(6)
C7 C24 1.535(6)
C7 C22 1.531(6)
C7 C6 1.553(5)
C11 C10 1.374(7)
C11 C12 1.400(7)
C10 C4 1.523(6)
C16 C17 1.404(6)
C14 C13 1.381(7)
C4 C5 1.537(6)
C4 C3 1.517(6)
C20 C19 1.379(7)
C5 C6 1.523(6)
C5 C1 1.525(6)
C3 C2 1.514(6)
C2 C1 1.545(6)
C13 C12 1.397(7)
C19 C18 1.382(7)
C17 C18 1.395(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350732
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.500 0.000 0.000 97.3 16.1
