#------------------------------------------------------------------------------
#$Date: 2022-09-28 00:54:06 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278223 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/07/7130778.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_7130778
loop_
_publ_author_name
'Fernandes, Rodney Agustinho'
'Kumar, Atul'
'Pathare, Ramdas Shivaji'
_publ_section_title
;
 Asymmetric Total Synthesis of (+)-Dihydroitomanallene B and Formal
 Synthesis of (-)-Kumausallene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04574E
_journal_year                    2022
_chemical_formula_moiety         'C22 H21 N2 O9'
_chemical_formula_sum            'C22 H21 N2 O9'
_chemical_formula_weight         457.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-16 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.911(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0311(7)
_cell_length_b                   41.153(3)
_cell_length_c                   7.9883(11)
_cell_measurement_reflns_used    3066
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.8410
_cell_measurement_theta_min      2.8060
_cell_volume                     2129.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   1.00   16.00    --  -20.00   0.00-108.00  180
  2  ω   -107.00 -72.00   1.00   16.00    --  -20.00 -72.00-180.00   35
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.1479
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8643
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.979
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0849
_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)+(0.1575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2095
_refine_ls_wR_factor_ref         0.3167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1844
_reflns_number_total             3679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04574e2.cif
_cod_data_source_block           raf-ram-061_mo
_cod_original_cell_volume        2129.1(4)
_cod_database_code               7130778
_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   0.990
_shelx_estimated_absorpt_t_min   0.979
_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:
 C00L(H00L), C00T(H00T), C00U(H00U)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00R(H00D,H00E), C00S(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00W(H00W), C00X(H00X)
2.d Idealised Me refined as rotating group:
 C00V(H00J,H00K,H00Q)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O001 O 0.4736(5) 0.57769(8) 0.5297(5) 0.0278(10) Uani 1 1 d . . . . .
O002 O 0.2888(6) 0.60068(9) 0.0855(5) 0.0302(10) Uani 1 1 d . . . . .
O003 O 0.1524(5) 0.66956(8) 0.1001(5) 0.0284(10) Uani 1 1 d . . . . .
O004 O 0.7767(6) 0.55098(9) 0.6336(6) 0.0374(11) Uani 1 1 d . . . . .
O005 O -0.1357(6) 0.69804(10) 0.0573(7) 0.0473(13) Uani 1 1 d . . . . .
O006 O 0.6529(7) 0.80424(10) -0.0139(7) 0.0474(13) Uani 1 1 d . . . . .
O007 O 0.3876(7) 0.83392(10) -0.0458(7) 0.0466(12) Uani 1 1 d . . . . .
O008 O 0.0250(7) 0.46025(10) 0.8595(7) 0.0542(14) Uani 1 1 d . . . . .
N009 N 0.1934(7) 0.45446(12) 0.8539(7) 0.0340(13) Uani 1 1 d . . . . .
N00A N 0.4774(8) 0.80766(12) -0.0200(7) 0.0379(13) Uani 1 1 d . . . . .
O00B O 0.2766(7) 0.42817(11) 0.8977(8) 0.0609(16) Uani 1 1 d . . . . .
C00C C 0.4970(8) 0.47499(13) 0.8113(8) 0.0255(13) Uani 1 1 d . . . . .
H00C H 0.566947 0.455301 0.860501 0.031 Uiso 1 1 calc R . . . .
C00D C 0.5990(9) 0.55299(13) 0.6144(8) 0.0269(13) Uani 1 1 d . . . . .
C00E C 0.0401(9) 0.69681(13) 0.0695(9) 0.0337(15) Uani 1 1 d . . . . .
C00F C 0.2965(8) 0.48021(13) 0.7952(8) 0.0277(13) Uani 1 1 d . . . . .
C00G C 0.2840(8) 0.53232(13) 0.6634(8) 0.0274(14) Uani 1 1 d . . . . .
H00G H 0.211921 0.551704 0.611234 0.033 Uiso 1 1 calc R . . . .
C00H C 0.1593(8) 0.72533(13) 0.0491(8) 0.0285(14) Uani 1 1 d . . . . .
C00I C 0.5928(8) 0.49938(13) 0.7535(8) 0.0286(14) Uani 1 1 d . . . . .
H00I H 0.731283 0.496703 0.764180 0.034 Uiso 1 1 calc R . . . .
C00J C 0.3692(9) 0.77872(13) 0.0067(8) 0.0298(14) Uani 1 1 d . . . . .
C00K C 0.4860(8) 0.52786(13) 0.6797(8) 0.0263(13) Uani 1 1 d . . . . .
C00L C 0.0509(8) 0.63906(13) 0.1101(8) 0.0288(14) Uani 1 1 d . . . . .
H00L H -0.054344 0.641901 0.164476 0.035 Uiso 1 1 calc R . . . .
C00M C 0.1843(9) 0.78355(14) 0.0276(9) 0.0386(17) Uani 1 1 d . . . . .
H00M H 0.131503 0.804799 0.027567 0.046 Uiso 1 1 calc R . . . .
C00N C 0.1883(8) 0.50833(14) 0.7238(8) 0.0320(15) Uani 1 1 d . . . . .
H00N H 0.051139 0.511141 0.716337 0.038 Uiso 1 1 calc R . . . .
C00O C 0.2444(9) 0.62541(16) -0.2010(9) 0.0419(17) Uani 1 1 d . . . . .
H00O H 0.165991 0.628770 -0.326824 0.050 Uiso 1 1 calc R . . . .
C00P C 0.0795(8) 0.75646(14) 0.0484(9) 0.0378(16) Uani 1 1 d . . . . .
H00P H -0.047866 0.759012 0.062310 0.045 Uiso 1 1 calc R . . . .
C00Q C 0.5661(9) 0.60279(12) 0.4582(8) 0.0296(14) Uani 1 1 d . . . . .
H00A H 0.614560 0.593512 0.367417 0.035 Uiso 1 1 calc R . . . .
H00B H 0.685428 0.612704 0.557373 0.035 Uiso 1 1 calc R . . . .
C00R C -0.0403(8) 0.62425(13) -0.0795(8) 0.0281(14) Uani 1 1 d . . . . .
H00D H -0.096725 0.641300 -0.173369 0.034 Uiso 1 1 calc R . . . .
H00E H -0.151413 0.608596 -0.090257 0.034 Uiso 1 1 calc R . . . .
C00S C 0.4003(8) 0.62793(12) 0.3707(8) 0.0269(13) Uani 1 1 d . . . . .
H00F H 0.353238 0.636572 0.463801 0.032 Uiso 1 1 calc R . . . .
H00H H 0.460872 0.646204 0.327590 0.032 Uiso 1 1 calc R . . . .
C00T C 0.1471(8) 0.60674(15) -0.0984(8) 0.0332(15) Uani 1 1 d . . . . .
H00T H 0.099264 0.585415 -0.160638 0.040 Uiso 1 1 calc R . . . .
C00U C 0.2166(8) 0.61519(13) 0.2139(8) 0.0267(13) Uani 1 1 d . . . . .
H00U H 0.151670 0.597705 0.260858 0.032 Uiso 1 1 calc R . . . .
C00V C 0.4337(9) 0.63795(16) -0.1312(9) 0.0430(17) Uani 1 1 d . . . . .
H00J H 0.508675 0.631902 -0.207463 0.064 Uiso 1 1 calc GR . . . .
H00K H 0.507226 0.629514 -0.008006 0.064 Uiso 1 1 calc GR . . . .
H00Q H 0.424719 0.661680 -0.126831 0.064 Uiso 1 1 calc GR . . . .
C00W C 0.3485(9) 0.72170(14) 0.0292(9) 0.0355(16) Uani 1 1 d . . . . .
H00W H 0.403467 0.700610 0.029209 0.043 Uiso 1 1 calc R . . . .
C00X C 0.4538(8) 0.74865(14) 0.0096(8) 0.0338(15) Uani 1 1 d . . . . .
H00X H 0.582795 0.746434 -0.001589 0.041 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
C00D O001 C00Q 115.5(4) . . ?
C00U O002 C00T 111.0(4) . . ?
C00E O003 C00L 117.6(4) . . ?
O008 N009 C00F 118.6(5) . . ?
O00B N009 O008 121.8(5) . . ?
O00B N009 C00F 119.6(5) . . ?
O006 N00A O007 123.5(5) . . ?
O006 N00A C00J 118.1(5) . . ?
O007 N00A C00J 118.4(5) . . ?
C00F C00C H00C 121.1 . . ?
C00F C00C C00I 117.9(5) . . ?
C00I C00C H00C 121.1 . . ?
O001 C00D C00K 111.1(5) . . ?
O004 C00D O001 124.2(5) . . ?
O004 C00D C00K 124.6(5) . . ?
O003 C00E C00H 111.3(5) . . ?
O005 C00E O003 124.4(5) . . ?
O005 C00E C00H 124.3(5) . . ?
C00C C00F N009 118.3(5) . . ?
C00N C00F N009 118.6(5) . . ?
C00N C00F C00C 123.2(5) . . ?
C00K C00G H00G 120.3 . . ?
C00N C00G H00G 120.3 . . ?
C00N C00G C00K 119.5(5) . . ?
C00P C00H C00E 118.8(5) . . ?
C00P C00H C00W 119.5(5) . . ?
C00W C00H C00E 121.7(5) . . ?
C00C C00I H00I 120.0 . . ?
C00C C00I C00K 119.9(5) . . ?
C00K C00I H00I 120.0 . . ?
C00M C00J N00A 117.5(5) . . ?
C00X C00J N00A 119.2(5) . . ?
C00X C00J C00M 123.2(5) . . ?
C00G C00K C00D 122.2(5) . . ?
C00G C00K C00I 121.0(5) . . ?
C00I C00K C00D 116.8(5) . . ?
O003 C00L H00L 112.5 . . ?
O003 C00L C00R 108.4(4) . . ?
O003 C00L C00U 107.5(4) . . ?
C00R C00L H00L 112.5 . . ?
C00U C00L H00L 112.5 . . ?
C00U C00L C00R 102.9(5) . . ?
C00J C00M H00M 121.1 . . ?
C00P C00M C00J 117.9(5) . . ?
C00P C00M H00M 121.1 . . ?
C00F C00N C00G 118.6(5) . . ?
C00F C00N H00N 120.7 . . ?
C00G C00N H00N 120.7 . . ?
C00T C00O H00O 117.4 . . ?
C00V C00O H00O 117.4 . . ?
C00V C00O C00T 125.1(6) . . ?
C00H C00P H00P 119.7 . . ?
C00M C00P C00H 120.5(5) . . ?
C00M C00P H00P 119.7 . . ?
O001 C00Q H00A 110.4 . . ?
O001 C00Q H00B 110.4 . . ?
O001 C00Q C00S 106.6(4) . . ?
H00A C00Q H00B 108.6 . . ?
C00S C00Q H00A 110.4 . . ?
C00S C00Q H00B 110.4 . . ?
C00L C00R H00D 111.0 . . ?
C00L C00R H00E 111.0 . . ?
C00L C00R C00T 103.7(4) . . ?
H00D C00R H00E 109.0 . . ?
C00T C00R H00D 111.0 . . ?
C00T C00R H00E 111.0 . . ?
C00Q C00S H00F 108.8 . . ?
C00Q C00S H00H 108.8 . . ?
H00F C00S H00H 107.7 . . ?
C00U C00S C00Q 113.9(4) . . ?
C00U C00S H00F 108.8 . . ?
C00U C00S H00H 108.8 . . ?
O002 C00T C00O 111.8(5) . . ?
O002 C00T C00R 104.9(4) . . ?
O002 C00T H00T 108.7 . . ?
C00O C00T C00R 114.0(5) . . ?
C00O C00T H00T 108.7 . . ?
C00R C00T H00T 108.7 . . ?
O002 C00U C00L 106.9(5) . . ?
O002 C00U C00S 108.2(4) . . ?
O002 C00U H00U 108.0 . . ?
C00L C00U H00U 108.0 . . ?
C00S C00U C00L 117.6(5) . . ?
C00S C00U H00U 108.0 . . ?
C00O C00V H00J 109.5 . . ?
C00O C00V H00K 109.5 . . ?
C00O C00V H00Q 109.5 . . ?
H00J C00V H00K 109.5 . . ?
H00J C00V H00Q 109.5 . . ?
H00K C00V H00Q 109.5 . . ?
C00H C00W H00W 120.0 . . ?
C00X C00W C00H 120.1(5) . . ?
C00X C00W H00W 120.0 . . ?
C00J C00X C00W 118.8(5) . . ?
C00J C00X H00X 120.6 . . ?
C00W C00X H00X 120.6 . . ?
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 C00D 1.343(6) . ?
O001 C00Q 1.451(6) . ?
O002 C00T 1.440(7) . ?
O002 C00U 1.440(6) . ?
O003 C00E 1.338(6) . ?
O003 C00L 1.462(6) . ?
O004 C00D 1.201(6) . ?
O005 C00E 1.202(7) . ?
O006 N00A 1.224(6) . ?
O007 N00A 1.228(6) . ?
O008 N009 1.226(6) . ?
N009 O00B 1.215(6) . ?
N009 C00F 1.461(7) . ?
N00A C00J 1.472(7) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.382(7) . ?
C00C C00I 1.384(7) . ?
C00D C00K 1.515(8) . ?
C00E C00H 1.488(8) . ?
C00F C00N 1.380(7) . ?
C00G H00G 0.9500 . ?
C00G C00K 1.387(7) . ?
C00G C00N 1.383(7) . ?
C00H C00P 1.398(7) . ?
C00H C00W 1.408(8) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.393(7) . ?
C00J C00M 1.388(8) . ?
C00J C00X 1.369(7) . ?
C00L H00L 1.0000 . ?
C00L C00R 1.523(8) . ?
C00L C00U 1.503(7) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.382(8) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00O C00T 1.472(8) . ?
C00O C00V 1.331(8) . ?
C00P H00P 0.9500 . ?
C00Q H00A 0.9900 . ?
C00Q H00B 0.9900 . ?
C00Q C00S 1.511(7) . ?
C00R H00D 0.9900 . ?
C00R H00E 0.9900 . ?
C00R C00T 1.560(8) . ?
C00S H00F 0.9900 . ?
C00S H00H 0.9900 . ?
C00S C00U 1.501(8) . ?
C00T H00T 1.0000 . ?
C00U H00U 1.0000 . ?
C00V H00J 0.9800 . ?
C00V H00K 0.9800 . ?
C00V H00Q 0.9800 . ?
C00W H00W 0.9500 . ?
C00W C00X 1.376(8) . ?
C00X H00X 0.9500 . ?
