#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:27:13 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157450.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_7157450
loop_
_publ_author_name
'Lu, Tianyu'
'Zhang, Xuange'
'Miao, Zhiwei'
_publ_section_title
;
 Synthesis of methylene cyclopropane-fused chromenes and dihydroquinolines
 by sequential [4 + 2]- and [1 + 2]-annulation.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3303
_journal_page_last               3311
_journal_paper_doi               10.1039/d0ob00389a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C25 H18 O3'
_chemical_formula_weight         366.39
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc21fpls
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-10 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                100.86(3)
_cell_angle_beta                 104.43(3)
_cell_angle_gamma                105.69(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5548(19)
_cell_length_b                   10.071(2)
_cell_length_c                   10.634(2)
_cell_measurement_reflns_used    2617
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8944
_cell_measurement_theta_min      2.0564
_cell_volume                     917.5(4)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11084
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.895
_diffrn_reflns_theta_min         2.184
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0960P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3137
_reflns_number_total             4356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00389a2.cif
_cod_data_source_block           shelxl_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157449--7157450.cif.
;
_cod_original_cell_volume        917.4(4)
_cod_database_code               7157450
_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_min   0.983
_shelx_estimated_absorpt_t_max   0.990
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20289(13) 0.37807(12) 0.32505(13) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.27703(15) -0.08047(14) 0.48622(13) 0.0383(4) Uani 1 1 d . . . . .
O3 O 0.14301(14) 0.11215(13) 0.12538(12) 0.0304(3) Uani 1 1 d . . . . .
C1 C -0.0054(2) 0.2911(2) 0.3953(2) 0.0386(5) Uani 1 1 d . . . . .
H1A H -0.041544 0.363841 0.368509 0.046 Uiso 1 1 calc R U . . .
H1B H -0.062795 0.226093 0.432816 0.046 Uiso 1 1 calc R U . . .
C2 C 0.1248(2) 0.28043(18) 0.38022(18) 0.0277(4) Uani 1 1 d . . . . .
C3 C 0.1943(2) 0.17752(18) 0.42741(18) 0.0272(4) Uani 1 1 d . . . . .
H3 H 0.163479 0.146807 0.503461 0.033 Uiso 1 1 calc R U . . .
C4 C 0.35925(19) 0.19667(18) 0.43900(17) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.423765 0.182064 0.521535 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4341(2) 0.31190(17) 0.38413(16) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.5862(2) 0.34085(18) 0.38598(18) 0.0281(4) Uani 1 1 d . . . . .
H6 H 0.643939 0.286465 0.423850 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6543(2) 0.44791(19) 0.33332(19) 0.0305(4) Uani 1 1 d . . . . .
H7 H 0.758306 0.467798 0.336537 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5692(2) 0.52529(18) 0.27617(18) 0.0307(4) Uani 1 1 d . . . . .
H8 H 0.614709 0.597366 0.238475 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4178(2) 0.49872(19) 0.27331(18) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.359751 0.552335 0.234409 0.034 Uiso 1 1 calc R U . . .
C10 C 0.35296(18) 0.39271(17) 0.32813(17) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.23309(19) 0.06351(18) 0.33657(17) 0.0250(4) Uani 1 1 d . . . . .
C12 C 0.2040(2) -0.07462(19) 0.37638(18) 0.0275(4) Uani 1 1 d . . . . .
C13 C 0.0800(2) -0.20267(18) 0.27733(18) 0.0264(4) Uani 1 1 d . . . . .
C14 C 0.0903(2) -0.33954(19) 0.27242(18) 0.0291(4) Uani 1 1 d . . . . .
H14 H 0.172641 -0.350706 0.336206 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0188(2) -0.4585(2) 0.17525(19) 0.0323(4) Uani 1 1 d . . . . .
H15 H -0.010202 -0.550913 0.170805 0.039 Uiso 1 1 calc R U . . .
C16 C -0.1406(2) -0.4423(2) 0.0845(2) 0.0360(5) Uani 1 1 d . . . . .
H16 H -0.215451 -0.524043 0.017641 0.043 Uiso 1 1 calc R U . . .
C17 C -0.1543(2) -0.3089(2) 0.0900(2) 0.0386(5) Uani 1 1 d . . . . .
H17 H -0.239078 -0.299207 0.027856 0.046 Uiso 1 1 calc R U . . .
C18 C -0.0447(2) -0.1887(2) 0.1862(2) 0.0329(4) Uani 1 1 d . . . . .
H18 H -0.054502 -0.096759 0.190087 0.040 Uiso 1 1 calc R U . . .
C19 C 0.21619(18) 0.05174(17) 0.19000(17) 0.0238(4) Uani 1 1 d . . . . .
C20 C 0.29858(19) -0.03632(17) 0.12974(17) 0.0247(4) Uani 1 1 d . . . . .
C21 C 0.2448(2) -0.09929(18) -0.00971(18) 0.0299(4) Uani 1 1 d . . . . .
H21 H 0.155896 -0.087946 -0.064195 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3220(2) -0.1784(2) -0.0680(2) 0.0362(5) Uani 1 1 d . . . . .
H22 H 0.285744 -0.220965 -0.162815 0.043 Uiso 1 1 calc R U . . .
C23 C 0.4508(2) -0.1959(2) 0.0102(2) 0.0395(5) Uani 1 1 d . . . . .
H23 H 0.502599 -0.250378 -0.030947 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5052(2) -0.1340(2) 0.1490(2) 0.0356(5) Uani 1 1 d . . . . .
H24 H 0.594172 -0.146048 0.202544 0.043 Uiso 1 1 calc R U . . .
C25 C 0.4292(2) -0.05457(19) 0.20920(19) 0.0291(4) Uani 1 1 d . . . . .
H25 H 0.465693 -0.012722 0.304103 0.035 Uiso 1 1 calc R U . . .
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'
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
C2 O1 C10 121.29(13) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 O1 117.26(16) . . ?
C1 C2 C3 123.50(17) . . ?
O1 C2 C3 119.10(14) . . ?
C2 C3 C4 119.86(14) . . ?
C2 C3 C11 124.75(15) . . ?
C4 C3 C11 60.49(11) . . ?
C2 C3 H3 113.8 . . ?
C4 C3 H3 113.8 . . ?
C11 C3 H3 113.8 . . ?
C5 C4 C3 115.08(14) . . ?
C5 C4 C11 116.96(14) . . ?
C3 C4 C11 60.95(11) . . ?
C5 C4 H4 117.3 . . ?
C3 C4 H4 117.3 . . ?
C11 C4 H4 117.3 . . ?
C10 C5 C6 118.14(16) . . ?
C10 C5 C4 120.23(15) . . ?
C6 C5 C4 121.63(15) . . ?
C7 C6 C5 121.03(16) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.39(16) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.67(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.92(16) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C5 C10 C9 121.84(16) . . ?
C5 C10 O1 123.60(15) . . ?
C9 C10 O1 114.54(15) . . ?
C12 C11 C19 116.49(15) . . ?
C12 C11 C4 117.27(15) . . ?
C19 C11 C4 116.30(14) . . ?
C12 C11 C3 112.03(14) . . ?
C19 C11 C3 123.77(15) . . ?
C4 C11 C3 58.56(11) . . ?
O2 C12 C13 121.68(16) . . ?
O2 C12 C11 121.39(16) . . ?
C13 C12 C11 116.92(15) . . ?
C18 C13 C14 119.12(17) . . ?
C18 C13 C12 121.15(16) . . ?
C14 C13 C12 119.71(16) . . ?
C15 C14 C13 120.33(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.70(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.67(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.09(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.05(18) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O3 C19 C20 122.08(16) . . ?
O3 C19 C11 122.37(16) . . ?
C20 C19 C11 115.53(15) . . ?
C21 C20 C25 119.70(16) . . ?
C21 C20 C19 118.75(16) . . ?
C25 C20 C19 121.54(16) . . ?
C22 C21 C20 119.63(18) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.63(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.29(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.88(19) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 119.88(18) . . ?
C24 C25 H25 120.1 . . ?
C20 C25 H25 120.1 . . ?
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 C2 1.381(2) . ?
O1 C10 1.3926(19) . ?
O2 C12 1.223(2) . ?
O3 C19 1.216(2) . ?
C1 C2 1.323(2) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.473(2) . ?
C3 C4 1.506(2) . ?
C3 C11 1.543(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.488(2) . ?
C4 C11 1.536(2) . ?
C4 H4 1.0000 . ?
C5 C10 1.383(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.504(2) . ?
C11 C19 1.505(2) . ?
C12 C13 1.489(3) . ?
C13 C18 1.394(2) . ?
C13 C14 1.400(2) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.494(2) . ?
C20 C21 1.398(2) . ?
C20 C25 1.400(2) . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1B O2 0.95 2.61 3.533(3) 164.1 2_556 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O1 C2 C1 167.98(16) . . . . ?
C10 O1 C2 C3 -7.9(2) . . . . ?
C1 C2 C3 C4 -164.37(17) . . . . ?
O1 C2 C3 C4 11.2(2) . . . . ?
C1 C2 C3 C11 122.7(2) . . . . ?
O1 C2 C3 C11 -61.7(2) . . . . ?
C2 C3 C4 C5 -7.3(2) . . . . ?
C11 C3 C4 C5 108.22(16) . . . . ?
C2 C3 C4 C11 -115.48(18) . . . . ?
C3 C4 C5 C10 0.2(2) . . . . ?
C11 C4 C5 C10 68.9(2) . . . . ?
C3 C4 C5 C6 -179.06(15) . . . . ?
C11 C4 C5 C6 -110.37(18) . . . . ?
C10 C5 C6 C7 0.1(2) . . . . ?
C4 C5 C6 C7 179.42(15) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C6 C5 C10 C9 0.8(2) . . . . ?
C4 C5 C10 C9 -178.52(15) . . . . ?
C6 C5 C10 O1 -177.39(14) . . . . ?
C4 C5 C10 O1 3.3(2) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C8 C9 C10 O1 177.64(14) . . . . ?
C2 O1 C10 C5 0.6(2) . . . . ?
C2 O1 C10 C9 -177.70(15) . . . . ?
C5 C4 C11 C12 154.50(15) . . . . ?
C3 C4 C11 C12 -100.34(16) . . . . ?
C5 C4 C11 C19 10.0(2) . . . . ?
C3 C4 C11 C19 115.12(17) . . . . ?
C5 C4 C11 C3 -105.16(16) . . . . ?
C2 C3 C11 C12 -142.94(17) . . . . ?
C4 C3 C11 C12 109.38(16) . . . . ?
C2 C3 C11 C19 5.2(3) . . . . ?
C4 C3 C11 C19 -102.47(17) . . . . ?
C2 C3 C11 C4 107.68(18) . . . . ?
C19 C11 C12 O2 144.99(17) . . . . ?
C4 C11 C12 O2 0.5(2) . . . . ?
C3 C11 C12 O2 -64.4(2) . . . . ?
C19 C11 C12 C13 -36.4(2) . . . . ?
C4 C11 C12 C13 179.14(14) . . . . ?
C3 C11 C12 C13 114.26(17) . . . . ?
O2 C12 C13 C18 150.35(19) . . . . ?
C11 C12 C13 C18 -28.3(2) . . . . ?
O2 C12 C13 C14 -31.5(3) . . . . ?
C11 C12 C13 C14 149.87(16) . . . . ?
C18 C13 C14 C15 2.4(3) . . . . ?
C12 C13 C14 C15 -175.78(16) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C14 C13 C18 C17 -1.7(3) . . . . ?
C12 C13 C18 C17 176.43(17) . . . . ?
C12 C11 C19 O3 132.00(17) . . . . ?
C4 C11 C19 O3 -83.2(2) . . . . ?
C3 C11 C19 O3 -14.9(2) . . . . ?
C12 C11 C19 C20 -49.4(2) . . . . ?
C4 C11 C19 C20 95.38(18) . . . . ?
C3 C11 C19 C20 163.69(15) . . . . ?
O3 C19 C20 C21 -26.3(2) . . . . ?
C11 C19 C20 C21 155.18(15) . . . . ?
O3 C19 C20 C25 152.52(16) . . . . ?
C11 C19 C20 C25 -26.0(2) . . . . ?
C25 C20 C21 C22 -0.4(3) . . . . ?
C19 C20 C21 C22 178.37(15) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C20 -0.4(3) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C19 C20 C25 C24 -178.23(15) . . . . ?
