#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/54/7245456.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_7245456
loop_
_publ_author_name
'Nie, Chang-Rui'
'Zhao, Hong-Ping'
'Liang, Wang-Fu'
'Zhong, Xin-Xian'
'Liang, Cui'
'Su, Gui-Fa'
'Mo, Dong-Liang'
_publ_section_title
;
 Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to
 prepare pentacyclic chromeno[4,3-b]indolines
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              6854
_journal_page_last               6859
_journal_paper_doi               10.1039/D2GC02225G
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C30 H25 N O2'
_chemical_formula_sum            'C30 H25 N O2'
_chemical_formula_weight         431.53
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-09 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                99.033(4)
_cell_angle_beta                 97.884(4)
_cell_angle_gamma                107.657(4)
_cell_formula_units_Z            2
_cell_length_a                   9.206(3)
_cell_length_b                   10.087(3)
_cell_length_c                   13.161(4)
_cell_measurement_reflns_used    5487
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.37
_cell_volume                     1127.7(6)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14151
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.783
_diffrn_reflns_theta_min         1.598
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0417
_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)+(0.0659P)²+0.2182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3807
_reflns_number_total             4768
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc02225g2.cif
_cod_data_source_block           aaaa
_cod_depositor_comments
;
          Adding full bibliography for 7245456.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.61 H2.17 N0.09 O0.17'
_cod_original_formula_weight         37.52
_cod_original_formula_moiety         '0.09(C30 H25 N O2)'
_cod_original_formula_units_Z            23
_cod_original_cell_volume        1127.8(5)
_cod_database_code               7245456
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N003(H003)
2.b Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
2.c Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00C), C00K(H00I,H00K)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O001 O 0.22852(14) 0.30014(12) 0.39797(8) 0.0488(3) Uani 1 1 d . . . . .
O002 O 0.38412(12) 0.67079(11) 0.28162(9) 0.0496(3) Uani 1 1 d . . . . .
N003 N 0.14113(13) 0.40908(12) 0.11561(9) 0.0335(3) Uani 1 1 d . . . . .
H003 H 0.1480 0.3546 0.0605 0.040 Uiso 1 1 d R . . . .
C004 C 0.27789(14) 0.28148(14) 0.22000(10) 0.0306(3) Uani 1 1 d . . . . .
C005 C 0.25526(14) 0.42215(14) 0.21091(10) 0.0302(3) Uani 1 1 d . . . . .
C006 C 0.00584(15) 0.40251(14) 0.25056(11) 0.0331(3) Uani 1 1 d . . . . .
C007 C 0.17590(15) 0.47317(14) 0.29814(10) 0.0319(3) Uani 1 1 d . . . . .
C008 C -0.00655(15) 0.37113(14) 0.14149(11) 0.0333(3) Uani 1 1 d . . . . .
C009 C 0.21629(16) 0.73256(14) 0.39380(11) 0.0352(3) Uani 1 1 d . . . . .
C00A C 0.30542(15) 0.19581(15) 0.13607(11) 0.0364(3) Uani 1 1 d . . . . .
H00A H 0.3133 0.2273 0.0737 0.044 Uiso 1 1 calc R . . . .
C00B C 0.60839(16) 0.69674(14) 0.13571(10) 0.0330(3) Uani 1 1 d . . . . .
C00C C 0.26327(16) 0.22991(15) 0.31185(11) 0.0358(3) Uani 1 1 d . . . . .
C00D C 0.22791(16) 0.63536(14) 0.29808(11) 0.0357(3) Uani 1 1 d . . . . .
H00D H 0.1640 0.6485 0.2370 0.043 Uiso 1 1 calc R . . . .
C00E C 0.40828(15) 0.54777(14) 0.22533(11) 0.0335(3) Uani 1 1 d . . . . .
H00E H 0.4905 0.5276 0.2693 0.040 Uiso 1 1 calc R . . . .
C00F C -0.12637(17) 0.37550(15) 0.29366(13) 0.0400(3) Uani 1 1 d . . . . .
H00F H -0.1185 0.3951 0.3660 0.048 Uiso 1 1 calc R . . . .
C00G C 0.75067(17) 0.67500(16) 0.13938(12) 0.0417(3) Uani 1 1 d . . . . .
H00G H 0.7554 0.5838 0.1367 0.050 Uiso 1 1 calc R . . . .
C00H C 0.07238(18) 0.74748(16) 0.40088(12) 0.0423(3) Uani 1 1 d . . . . .
H00H H -0.0130 0.6976 0.3473 0.051 Uiso 1 1 calc R . . . .
C00I C 0.23784(18) 0.44499(16) 0.40241(11) 0.0396(3) Uani 1 1 d . . . . .
H00B H 0.3456 0.5053 0.4263 0.048 Uiso 1 1 calc R . . . .
H00C H 0.1796 0.4711 0.4537 0.048 Uiso 1 1 calc R . . . .
C00J C 0.27832(18) 0.09832(16) 0.31922(13) 0.0439(4) Uani 1 1 d . . . . .
H00J H 0.2685 0.0653 0.3809 0.053 Uiso 1 1 calc R . . . .
C00K C 0.45985(17) 0.57350(16) 0.12349(11) 0.0405(3) Uani 1 1 d . . . . .
H00I H 0.4739 0.4877 0.0880 0.049 Uiso 1 1 calc R . . . .
H00K H 0.3774 0.5905 0.0787 0.049 Uiso 1 1 calc R . . . .
C00L C 0.60648(19) 0.83434(16) 0.14124(12) 0.0446(4) Uani 1 1 d . . . . .
H00L H 0.5127 0.8518 0.1396 0.053 Uiso 1 1 calc R . . . .
C00M C 0.32126(17) 0.06562(16) 0.14275(13) 0.0431(3) Uani 1 1 d . . . . .
H00M H 0.3409 0.0108 0.0859 0.052 Uiso 1 1 calc R . . . .
C00N C -0.27101(17) 0.31859(16) 0.22707(14) 0.0457(4) Uani 1 1 d . . . . .
H00N H -0.3608 0.2993 0.2550 0.055 Uiso 1 1 calc R . . . .
C00O C 0.30760(17) 0.01721(16) 0.23549(13) 0.0458(4) Uani 1 1 d . . . . .
H00O H 0.3183 -0.0703 0.2408 0.055 Uiso 1 1 calc R . . . .
C00P C -0.15077(16) 0.31631(15) 0.07457(12) 0.0408(3) Uani 1 1 d . . . . .
H00P H -0.1593 0.2974 0.0021 0.049 Uiso 1 1 calc R . . . .
C00Q C -0.28237(17) 0.29050(16) 0.11952(14) 0.0454(4) Uani 1 1 d . . . . .
H00Q H -0.3802 0.2535 0.0761 0.054 Uiso 1 1 calc R . . . .
C00R C 0.3414(2) 0.80815(18) 0.47406(13) 0.0497(4) Uani 1 1 d . . . . .
H00R H 0.4384 0.7992 0.4711 0.060 Uiso 1 1 calc R . . . .
C00S C 0.7420(2) 0.94647(16) 0.14921(14) 0.0554(4) Uani 1 1 d . . . . .
H00S H 0.7383 1.0382 0.1531 0.066 Uiso 1 1 calc R . . . .
C00T C 0.88600(18) 0.7879(2) 0.14696(14) 0.0525(4) Uani 1 1 d . . . . .
H00T H 0.9804 0.7717 0.1491 0.063 Uiso 1 1 calc R . . . .
C00U C 0.0550(2) 0.83559(18) 0.48652(14) 0.0520(4) Uani 1 1 d . . . . .
H00U H -0.0420 0.8438 0.4908 0.062 Uiso 1 1 calc R . . . .
C00V C 0.1808(3) 0.91105(19) 0.56531(13) 0.0591(5) Uani 1 1 d . . . . .
H00V H 0.1694 0.9712 0.6226 0.071 Uiso 1 1 calc R . . . .
C00W C 0.8813(2) 0.92322(19) 0.15133(14) 0.0559(4) Uani 1 1 d . . . . .
H00W H 0.9719 0.9985 0.1557 0.067 Uiso 1 1 calc R . . . .
C00X C 0.3230(2) 0.8975(2) 0.55921(14) 0.0610(5) Uani 1 1 d . . . . .
H00X H 0.4081 0.9486 0.6127 0.073 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 0.0033 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'
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
C00C O001 C00I 118.06(11) . . ?
C00D O002 C00E 110.13(10) . . ?
C005 N003 H003 114.4 . . ?
C008 N003 H003 114.2 . . ?
C008 N003 C005 107.43(10) . . ?
C00A C004 C005 121.66(12) . . ?
C00A C004 C00C 117.68(12) . . ?
C00C C004 C005 120.58(12) . . ?
N003 C005 C004 112.22(10) . . ?
N003 C005 C007 101.08(10) . . ?
N003 C005 C00E 113.16(10) . . ?
C004 C005 C007 111.72(10) . . ?
C004 C005 C00E 114.32(11) . . ?
C007 C005 C00E 103.17(10) . . ?
C008 C006 C007 107.04(11) . . ?
C00F C006 C007 132.47(13) . . ?
C00F C006 C008 120.34(13) . . ?
C005 C007 C00D 99.77(10) . . ?
C006 C007 C005 102.60(10) . . ?
C006 C007 C00D 110.79(11) . . ?
C006 C007 C00I 118.61(11) . . ?
C00I C007 C005 111.24(11) . . ?
C00I C007 C00D 111.80(11) . . ?
N003 C008 C006 110.52(12) . . ?
C00P C008 N003 128.45(13) . . ?
C00P C008 C006 120.97(13) . . ?
C00H C009 C00D 118.21(13) . . ?
C00R C009 C00D 123.26(13) . . ?
C00R C009 C00H 118.53(14) . . ?
C004 C00A H00A 119.0 . . ?
C00M C00A C004 121.96(13) . . ?
C00M C00A H00A 119.0 . . ?
C00G C00B C00K 121.02(13) . . ?
C00L C00B C00G 117.85(13) . . ?
C00L C00B C00K 121.11(13) . . ?
O001 C00C C004 123.50(13) . . ?
O001 C00C C00J 115.66(12) . . ?
C00J C00C C004 120.80(13) . . ?
O002 C00D C007 105.04(11) . . ?
O002 C00D C009 111.28(11) . . ?
O002 C00D H00D 107.8 . . ?
C007 C00D H00D 107.8 . . ?
C009 C00D C007 116.71(11) . . ?
C009 C00D H00D 107.8 . . ?
O002 C00E C005 106.56(10) . . ?
O002 C00E H00E 108.2 . . ?
O002 C00E C00K 111.44(12) . . ?
C005 C00E H00E 108.2 . . ?
C00K C00E C005 114.04(11) . . ?
C00K C00E H00E 108.2 . . ?
C006 C00F H00F 120.5 . . ?
C006 C00F C00N 118.91(15) . . ?
C00N C00F H00F 120.5 . . ?
C00B C00G H00G 119.6 . . ?
C00B C00G C00T 120.75(14) . . ?
C00T C00G H00G 119.6 . . ?
C009 C00H H00H 119.6 . . ?
C00U C00H C009 120.75(15) . . ?
C00U C00H H00H 119.6 . . ?
O001 C00I C007 113.54(11) . . ?
O001 C00I H00B 108.9 . . ?
O001 C00I H00C 108.9 . . ?
C007 C00I H00B 108.9 . . ?
C007 C00I H00C 108.9 . . ?
H00B C00I H00C 107.7 . . ?
C00C C00J H00J 119.9 . . ?
C00O C00J C00C 120.11(14) . . ?
C00O C00J H00J 119.9 . . ?
C00B C00K C00E 114.91(12) . . ?
C00B C00K H00I 108.5 . . ?
C00B C00K H00K 108.5 . . ?
C00E C00K H00I 108.5 . . ?
C00E C00K H00K 108.5 . . ?
H00I C00K H00K 107.5 . . ?
C00B C00L H00L 119.5 . . ?
C00B C00L C00S 121.07(15) . . ?
C00S C00L H00L 119.5 . . ?
C00A C00M H00M 120.4 . . ?
C00A C00M C00O 119.23(14) . . ?
C00O C00M H00M 120.4 . . ?
C00F C00N H00N 119.8 . . ?
C00Q C00N C00F 120.43(14) . . ?
C00Q C00N H00N 119.8 . . ?
C00J C00O C00M 120.22(14) . . ?
C00J C00O H00O 119.9 . . ?
C00M C00O H00O 119.9 . . ?
C008 C00P H00P 121.1 . . ?
C008 C00P C00Q 117.76(14) . . ?
C00Q C00P H00P 121.1 . . ?
C00N C00Q C00P 121.57(14) . . ?
C00N C00Q H00Q 119.2 . . ?
C00P C00Q H00Q 119.2 . . ?
C009 C00R H00R 119.9 . . ?
C009 C00R C00X 120.26(16) . . ?
C00X C00R H00R 119.9 . . ?
C00L C00S H00S 119.8 . . ?
C00W C00S C00L 120.47(15) . . ?
C00W C00S H00S 119.8 . . ?
C00G C00T H00T 119.8 . . ?
C00W C00T C00G 120.44(15) . . ?
C00W C00T H00T 119.8 . . ?
C00H C00U H00U 120.0 . . ?
C00V C00U C00H 120.04(16) . . ?
C00V C00U H00U 120.0 . . ?
C00U C00V H00V 120.1 . . ?
C00X C00V C00U 119.77(16) . . ?
C00X C00V H00V 120.1 . . ?
C00S C00W C00T 119.42(15) . . ?
C00S C00W H00W 120.3 . . ?
C00T C00W H00W 120.3 . . ?
C00R C00X H00X 119.7 . . ?
C00V C00X C00R 120.64(17) . . ?
C00V C00X H00X 119.7 . . ?
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
O001 C00C 1.3687(17) . ?
O001 C00I 1.4288(18) . ?
O002 C00D 1.4286(17) . ?
O002 C00E 1.4361(17) . ?
N003 H003 0.8601 . ?
N003 C005 1.4822(17) . ?
N003 C008 1.4011(17) . ?
C004 C005 1.5156(18) . ?
C004 C00A 1.3933(19) . ?
C004 C00C 1.3963(19) . ?
C005 C007 1.5456(17) . ?
C005 C00E 1.5474(18) . ?
C006 C007 1.5050(19) . ?
C006 C008 1.401(2) . ?
C006 C00F 1.3836(19) . ?
C007 C00D 1.5592(19) . ?
C007 C00I 1.515(2) . ?
C008 C00P 1.388(2) . ?
C009 C00D 1.5075(19) . ?
C009 C00H 1.392(2) . ?
C009 C00R 1.380(2) . ?
C00A H00A 0.9300 . ?
C00A C00M 1.379(2) . ?
C00B C00G 1.388(2) . ?
C00B C00K 1.5123(19) . ?
C00B C00L 1.384(2) . ?
C00C C00J 1.392(2) . ?
C00D H00D 0.9800 . ?
C00E H00E 0.9800 . ?
C00E C00K 1.5160(19) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.389(2) . ?
C00G H00G 0.9300 . ?
C00G C00T 1.389(2) . ?
C00H H00H 0.9300 . ?
C00H C00U 1.381(2) . ?
C00I H00B 0.9700 . ?
C00I H00C 0.9700 . ?
C00J H00J 0.9300 . ?
C00J C00O 1.374(2) . ?
C00K H00I 0.9700 . ?
C00K H00K 0.9700 . ?
C00L H00L 0.9300 . ?
C00L C00S 1.385(2) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.391(2) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.382(2) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.393(2) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00X 1.387(2) . ?
C00S H00S 0.9300 . ?
C00S C00W 1.369(3) . ?
C00T H00T 0.9300 . ?
C00T C00W 1.371(3) . ?
C00U H00U 0.9300 . ?
C00U C00V 1.372(3) . ?
C00V H00V 0.9300 . ?
C00V C00X 1.369(3) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
