#------------------------------------------------------------------------------
#$Date: 2020-07-02 03:03:47 +0300 (Thu, 02 Jul 2020) $
#$Revision: 253640 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/84/1558461.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_1558461
loop_
_publ_author_name
'Banwell, Martin G.'
'Liu, Xin'
'Connal, Luke A.'
'Gardiner, Michael G.'
_publ_section_title
;
 Synthesis of Functionally and Stereochemically Diverse Polymers via
 Ring-Opening Metathesis Polymerization of Derivatives of the
 Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial
 Scale
;
_journal_name_full               Macromolecules
_journal_paper_doi               10.1021/acs.macromol.0c01305
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.94700(10)
_cell_length_b                   7.51010(10)
_cell_length_c                   17.0105(3)
_cell_measurement_reflns_used    2673
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9420
_cell_measurement_theta_min      5.1900
_cell_volume                     887.48(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -102.00 -21.00   0.50    0.50    --  -36.66 -57.00 -60.00  162
  2  ω    -29.00  64.00   0.50    0.50    --   36.66 -19.00 120.00  186
  3  ω     33.00  88.00   0.50    0.50    --   36.66-125.00-150.00  110
  4  ω     98.00 127.00   0.50    2.11    --  111.00 -45.00  90.00   58
  5  ω     63.00 103.00   0.50    2.11    --  111.00 -95.00-180.00   80
  6  ω     62.00  91.00   0.50    2.11    --  111.00-111.00-120.00   58
  7  ω    138.00 166.00   0.50    2.11    --  111.00  30.00  60.00   56
  8  ω     90.00 125.00   0.50    2.11    --  111.00 -15.00-150.00   70
  9  ω    103.00 132.00   0.50    2.11    --  111.00 -30.00 120.00   58
 10  ω     68.00 100.00   0.50    2.11    --  111.00-111.00 -90.00   64
 11  ω     61.00 106.00   0.50    2.11    --  111.00 -95.00 120.00   90
 12  ω     96.00 145.00   0.50    2.11    --  111.00  45.00-180.00   98
 13  ω     40.00  88.00   0.50    2.11    --  111.00 -15.00-150.00   96
 14  ω     46.00  72.00   0.50    2.11    --  111.00 -30.00 120.00   52
 15  ω     93.00 131.00   0.50    2.11    --  111.00  30.00  60.00   76
 16  ω     44.00 125.00   0.50    2.11    --  111.00 -45.00-180.00  162
 17  ω     44.00  95.00   0.50    2.11    --  111.00 -45.00  90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0846523000
_diffrn_orient_matrix_UB_12      0.1893019000
_diffrn_orient_matrix_UB_13      0.0044795000
_diffrn_orient_matrix_UB_21      0.2046391000
_diffrn_orient_matrix_UB_22      0.0780400000
_diffrn_orient_matrix_UB_23      0.0046999000
_diffrn_orient_matrix_UB_31      0.0063298000
_diffrn_orient_matrix_UB_32      0.0133119000
_diffrn_orient_matrix_UB_33      -0.0903929000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3577
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.088
_diffrn_reflns_theta_min         5.200
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (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    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 705 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0280
_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)+(0.0412P)²+0.1241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1755
_reflns_number_total             1799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma0c01305_si_002.cif
_cod_data_source_block           xl-4-95-2scaled
_cod_database_code               1558461
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H12 O3'
_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.
;
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
;
_ins_header
;
TITL XL-4-95-2scaled in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   6.947023   7.510143  17.010516  90.0000  90.0000  90.0000
ZERR    4.00   0.000130   0.000128   0.000306   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H O
UNIT 44.00 48.00 12.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-02-04
_olex2_date_sample_submission    2020-02-03
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGen holder with oil'
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.901
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.75729(16) 0.59754(14) 0.35552(7) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.92465(17) 0.56902(17) 0.46879(7) 0.0260(3) Uani 1 1 d . . . . .
O3 O 0.35277(17) 0.38021(19) 0.41671(8) 0.0307(3) Uani 1 1 d . . . . .
C1 C 0.7327(3) 0.6155(3) 0.49129(11) 0.0310(4) Uani 1 1 d . . . . .
H1A H 0.726156 0.738449 0.508611 0.037 Uiso 1 1 calc R . . . .
H1B H 0.686997 0.539018 0.533266 0.037 Uiso 1 1 calc R . . . .
C2 C 0.6143(2) 0.5877(2) 0.41607(9) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.516340 0.680508 0.409770 0.027 Uiso 1 1 calc R . . . .
C3 C 0.5259(2) 0.4029(2) 0.41363(8) 0.0195(3) Uani 1 1 d . . . . .
C4 C 0.6675(2) 0.2500(2) 0.40908(8) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.666902 0.186732 0.459479 0.020 Uiso 1 1 calc R . . . .
C5 C 0.6156(2) 0.1145(2) 0.34207(10) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.509154 0.032594 0.353162 0.028 Uiso 1 1 calc R . . . .
C6 C 0.5979(2) 0.2237(2) 0.26778(9) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.485033 0.247327 0.240271 0.030 Uiso 1 1 calc R . . . .
C7 C 0.7744(2) 0.2800(2) 0.24899(9) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.806199 0.351553 0.206295 0.028 Uiso 1 1 calc R . . . .
C8 C 0.9139(2) 0.2067(2) 0.30948(9) 0.0195(3) Uani 1 1 d . . . . .
H8 H 1.048451 0.198137 0.292556 0.023 Uiso 1 1 calc R . . . .
C9 C 0.8142(3) 0.0284(2) 0.32893(11) 0.0258(4) Uani 1 1 d . . . . .
H9A H 0.815475 -0.054714 0.285267 0.031 Uiso 1 1 calc R . . . .
H9B H 0.865090 -0.027757 0.375892 0.031 Uiso 1 1 calc R . . . .
C10 C 0.8791(2) 0.30458(19) 0.38918(9) 0.0156(3) Uani 1 1 d . . . . .
H10 H 0.963700 0.250580 0.428640 0.019 Uiso 1 1 calc R . . . .
C11 C 0.9142(2) 0.50456(19) 0.38985(9) 0.0181(3) Uani 1 1 d . . . . .
H11 H 1.033575 0.532503 0.361720 0.022 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0277
0 0 -1 0.0277
-4 1 2 0.0567
1 -5 1 0.0708
3 3 1 0.0682
-1 4 4 0.0675
2 -1 1 0.0790
-1 -5 1 0.0802
-4 0 -1 0.0683
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
C11 O1 C2 102.20(11) . . ?
C11 O2 C1 106.67(12) . . ?
O2 C1 C2 104.06(13) . . ?
O1 C2 C1 102.75(13) . . ?
O1 C2 C3 107.92(12) . . ?
C3 C2 C1 111.32(14) . . ?
O3 C3 C2 121.77(15) . . ?
O3 C3 C4 122.59(16) . . ?
C4 C3 C2 115.62(13) . . ?
C3 C4 C5 112.31(13) . . ?
C3 C4 C10 115.01(13) . . ?
C10 C4 C5 103.22(12) . . ?
C6 C5 C4 105.91(13) . . ?
C6 C5 C9 100.34(14) . . ?
C9 C5 C4 99.90(13) . . ?
C7 C6 C5 107.28(14) . . ?
C6 C7 C8 108.02(14) . . ?
C7 C8 C9 99.98(13) . . ?
C7 C8 C10 108.62(12) . . ?
C9 C8 C10 98.79(12) . . ?
C5 C9 C8 93.94(12) . . ?
C8 C10 C4 102.14(12) . . ?
C11 C10 C4 114.09(12) . . ?
C11 C10 C8 116.51(12) . . ?
O1 C11 O2 104.99(12) . . ?
O1 C11 C10 111.04(11) . . ?
O2 C11 C10 110.45(13) . . ?
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 1.4327(19) . ?
O1 C11 1.4203(18) . ?
O2 C1 1.431(2) . ?
O2 C11 1.4292(19) . ?
O3 C3 1.216(2) . ?
C1 C2 1.535(2) . ?
C2 C3 1.519(2) . ?
C3 C4 1.514(2) . ?
C4 C5 1.570(2) . ?
C4 C10 1.5635(19) . ?
C5 C6 1.511(2) . ?
C5 C9 1.540(2) . ?
C6 C7 1.336(2) . ?
C7 C8 1.517(2) . ?
C8 C9 1.544(2) . ?
C8 C10 1.5610(19) . ?
C10 C11 1.5217(19) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 0.0004 0.9991 0.0045 0.0047 -0.0903
-0.0001 -0.0004 -0.9991 -0.0045 -0.0047 0.0903
-3.9978 1.0015 2.0012 0.5370 -0.7306 -0.1929
1.0003 -4.9969 0.9976 -1.0261 -0.1806 -0.1504
2.9982 2.9974 0.9972 0.3181 0.8521 -0.0313
-0.9995 3.9993 3.9975 0.8596 0.1263 -0.3144
1.9992 -0.9997 0.9974 -0.3540 0.3358 -0.0908
-0.9986 -4.9962 0.9991 -0.8568 -0.5896 -0.1631
-3.9981 0.0010 -0.9961 0.3342 -0.8228 0.0647
