# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_6298
_audit_creation_date             11-02-14
_audit_creation_method           CRYSTALS_ver_14.18

_oxford_structure_analysis_title 6298
_chemical_name_systematic        .
_chemical_melting_point          .

_cell_length_a                   9.3781(1)
_cell_length_b                   8.1224(1)
_cell_length_c                   11.7374(1)
_cell_angle_alpha                90
_cell_angle_beta                 112.5315(14)
_cell_angle_gamma                90
_cell_volume                     825.824(17)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C15 H25 N1 O6 
# Dc =      1.27 Fooo =    340.00 Mu =      8.14 M =    315.37
# Found Formula = C15 H25 N1 O6 
# Dc =      1.27 FOOO =    340.00 Mu =      8.14 M =    315.37

_chemical_formula_sum            'C15 H25 N1 O6'
_chemical_formula_moiety         'C15 H25 N1 O6'
_chemical_compound_source        .
_chemical_formula_weight         315.37


_cell_measurement_reflns_used    41391
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.090
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_max          0.190

_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.814

# Sheldrick geometric approximatio 0.87 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd., (Oxford Diffraction, 2002)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            48681
_reflns_number_total             3443
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 3443 
# Number of reflections with Friedels Law is 1852 
# Theoretical number of reflections is about 1728 


_diffrn_reflns_theta_min         4.078
_diffrn_reflns_theta_max         76.179
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        76.179
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.23
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.17


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     1
_refine_ls_number_parameters     200
_oxford_refine_ls_R_factor_ref   0.0330
_refine_ls_wR_factor_ref         0.0902
_refine_ls_goodness_of_fit_ref   1.0050
_refine_ls_shift/su_max          0.0002414
_refine_ls_shift/su_mean         0.0000632


# The values computed from all data 
_oxford_reflns_number_all        3443
_refine_ls_R_factor_all          0.0330
_refine_ls_wR_factor_all         0.0902

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3390
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0896

_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_abs_structure_details 'Flack (1983), 1591 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.11P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.4862 0.6758 0.2588 0.0190 1.0000 Uani . . . . . .
C2 C 0.5736 0.8298 0.2937 0.0202 1.0000 Uani . . . . . .
O3 O 0.4766 0.9336 0.3320 0.0216 1.0000 Uani . . . . . .
C4 C 0.3183 0.8849 0.2705 0.0192 1.0000 Uani . . . . . .
C5 C 0.3275 0.6968 0.2496 0.0177 1.0000 Uani . . . . . .
C6 C 0.3173 0.5688 0.3463 0.0181 1.0000 Uani . . . . . .
C7 C 0.4210 0.4304 0.3316 0.0216 1.0000 Uani . . . . . .
C8 C 0.5495 0.5290 0.3155 0.0229 1.0000 Uani . . . . . .
C9 C 0.6204 0.9050 0.1932 0.0259 1.0000 Uani . . . . . .
C10 C 0.7362 0.7864 0.1738 0.0350 1.0000 Uani . . . . . .
C11 C 0.7009 1.0686 0.2417 0.0448 1.0000 Uani . . . . . .
C12 C 0.4843 0.9302 0.0709 0.0372 1.0000 Uani . . . . . .
C13 C 0.2236 0.9464 0.3411 0.0244 1.0000 Uani . . . . . .
C14 C 0.2138 0.6451 0.1209 0.0202 1.0000 Uani . . . . . .
O15 O 0.2388 0.5401 0.0589 0.0296 1.0000 Uani . . . . . .
O16 O 0.0801 0.7266 0.0882 0.0258 1.0000 Uani . . . . . .
C17 C -0.0380 0.6751 -0.0273 0.0365 1.0000 Uani . . . . . .
C18 C 0.1555 0.5144 0.3298 0.0222 1.0000 Uani . . . . . .
O19 O 0.1720 0.3864 0.4152 0.0290 1.0000 Uani . . . . . .
C20 C 0.0288 0.3362 0.4171 0.0417 1.0000 Uani . . . . . .
O21 O 0.6845 0.4928 0.3486 0.0316 1.0000 Uani . . . . . .
O22 O 0.3929 0.6431 0.4635 0.0216 1.0000 Uani . . . . . .
H21 H 0.6666 0.8046 0.3661 0.0236 1.0000 Uiso R . . . . .
H41 H 0.2784 0.9344 0.1878 0.0225 1.0000 Uiso R . . . . .
H71 H 0.4595 0.3603 0.4040 0.0263 1.0000 Uiso R . . . . .
H72 H 0.3659 0.3603 0.2612 0.0275 1.0000 Uiso R . . . . .
H102 H 0.7725 0.8333 0.1141 0.0529 1.0000 Uiso R . . . . .
H101 H 0.8239 0.7679 0.2481 0.0519 1.0000 Uiso R . . . . .
H103 H 0.6861 0.6804 0.1430 0.0540 1.0000 Uiso R . . . . .
H112 H 0.7409 1.1145 0.1834 0.0682 1.0000 Uiso R . . . . .
H111 H 0.7882 1.0532 0.3193 0.0678 1.0000 Uiso R . . . . .
H113 H 0.6299 1.1461 0.2538 0.0653 1.0000 Uiso R . . . . .
H122 H 0.5222 0.9623 0.0097 0.0547 1.0000 Uiso R . . . . .
H121 H 0.4137 1.0148 0.0776 0.0544 1.0000 Uiso R . . . . .
H123 H 0.4269 0.8324 0.0457 0.0562 1.0000 Uiso R . . . . .
H132 H 0.1149 0.9234 0.2947 0.0356 1.0000 Uiso R . . . . .
H131 H 0.2363 1.0641 0.3532 0.0374 1.0000 Uiso R . . . . .
H133 H 0.2596 0.8959 0.4226 0.0351 1.0000 Uiso R . . . . .
H172 H -0.1303 0.7380 -0.0372 0.0554 1.0000 Uiso R . . . . .
H171 H -0.0031 0.6895 -0.0938 0.0559 1.0000 Uiso R . . . . .
H173 H -0.0621 0.5607 -0.0221 0.0557 1.0000 Uiso R . . . . .
H182 H 0.0987 0.6064 0.3456 0.0287 1.0000 Uiso R . . . . .
H181 H 0.0976 0.4703 0.2434 0.0259 1.0000 Uiso R . . . . .
H201 H 0.0476 0.2438 0.4748 0.0608 1.0000 Uiso R . . . . .
H203 H -0.0198 0.4256 0.4446 0.0631 1.0000 Uiso R . . . . .
H202 H -0.0416 0.3033 0.3349 0.0611 1.0000 Uiso R . . . . .
H221 H 0.4263 0.5710 0.5196 0.0330 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          13.441
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.466 yes
N1 . C5 . 1.460 yes
N1 . C8 . 1.384 yes
C2 . O3 . 1.433 yes
C2 . C9 . 1.534 yes
C2 . H21 . 0.978 no
O3 . C4 . 1.435 yes
C4 . C5 . 1.555 yes
C4 . C13 . 1.513 yes
C4 . H41 . 0.983 no
C5 . C6 . 1.570 yes
C5 . C14 . 1.536 yes
C6 . C7 . 1.539 yes
C6 . C18 . 1.520 yes
C6 . O22 . 1.419 yes
C7 . C8 . 1.518 yes
C7 . H71 . 0.970 no
C7 . H72 . 0.973 no
C8 . O21 . 1.209 yes
C9 . C10 . 1.533 yes
C9 . C11 . 1.526 yes
C9 . C12 . 1.525 yes
C10 . H102 . 0.966 no
C10 . H101 . 0.954 no
C10 . H103 . 0.981 no
C11 . H112 . 0.972 no
C11 . H111 . 0.971 no
C11 . H113 . 0.965 no
C12 . H122 . 0.951 no
C12 . H121 . 0.979 no
C12 . H123 . 0.941 no
C13 . H132 . 0.972 no
C13 . H131 . 0.967 no
C13 . H133 . 0.974 no
C14 . O15 . 1.201 yes
C14 . O16 . 1.338 yes
O16 . C17 . 1.446 yes
C17 . H172 . 0.973 no
C17 . H171 . 0.962 no
C17 . H173 . 0.964 no
C18 . O19 . 1.411 yes
C18 . H182 . 0.975 no
C18 . H181 . 1.015 no
O19 . C20 . 1.412 yes
C20 . H201 . 0.981 no
C20 . H203 . 0.975 no
C20 . H202 . 0.974 no
O22 . H221 . 0.847 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 111.481 yes
C2 . N1 . C8 . 120.668 yes
C5 . N1 . C8 . 111.982 yes
N1 . C2 . O3 . 103.590 yes
N1 . C2 . C9 . 114.766 yes
O3 . C2 . C9 . 114.216 yes
N1 . C2 . H21 . 106.3 no
O3 . C2 . H21 . 108.3 no
C9 . C2 . H21 . 109.2 no
C2 . O3 . C4 . 109.827 yes
O3 . C4 . C5 . 103.944 yes
O3 . C4 . C13 . 110.176 yes
C5 . C4 . C13 . 119.379 yes
O3 . C4 . H41 . 108.3 no
C5 . C4 . H41 . 105.6 no
C13 . C4 . H41 . 108.9 no
C4 . C5 . N1 . 102.690 yes
C4 . C5 . C6 . 120.954 yes
N1 . C5 . C6 . 102.225 yes
C4 . C5 . C14 . 111.383 yes
N1 . C5 . C14 . 110.174 yes
C6 . C5 . C14 . 108.536 yes
C5 . C6 . C7 . 100.761 yes
C5 . C6 . C18 . 115.794 yes
C7 . C6 . C18 . 114.644 yes
C5 . C6 . O22 . 105.826 yes
C7 . C6 . O22 . 108.463 yes
C18 . C6 . O22 . 110.546 yes
C6 . C7 . C8 . 101.240 yes
C6 . C7 . H71 . 111.7 no
C8 . C7 . H71 . 111.9 no
C6 . C7 . H72 . 111.7 no
C8 . C7 . H72 . 113.0 no
H71 . C7 . H72 . 107.4 no
C7 . C8 . N1 . 107.417 yes
C7 . C8 . O21 . 127.953 yes
N1 . C8 . O21 . 124.583 yes
C2 . C9 . C10 . 106.968 yes
C2 . C9 . C11 . 107.782 yes
C10 . C9 . C11 . 108.992 yes
C2 . C9 . C12 . 113.212 yes
C10 . C9 . C12 . 109.232 yes
C11 . C9 . C12 . 110.521 yes
C9 . C10 . H102 . 109.0 no
C9 . C10 . H101 . 112.0 no
H102 . C10 . H101 . 107.8 no
C9 . C10 . H103 . 109.8 no
H102 . C10 . H103 . 109.3 no
H101 . C10 . H103 . 108.8 no
C9 . C11 . H112 . 109.9 no
C9 . C11 . H111 . 110.9 no
H112 . C11 . H111 . 107.2 no
C9 . C11 . H113 . 110.6 no
H112 . C11 . H113 . 109.1 no
H111 . C11 . H113 . 109.1 no
C9 . C12 . H122 . 109.1 no
C9 . C12 . H121 . 111.5 no
H122 . C12 . H121 . 109.1 no
C9 . C12 . H123 . 110.8 no
H122 . C12 . H123 . 109.1 no
H121 . C12 . H123 . 107.1 no
C4 . C13 . H132 . 109.9 no
C4 . C13 . H131 . 110.0 no
H132 . C13 . H131 . 108.4 no
C4 . C13 . H133 . 110.1 no
H132 . C13 . H133 . 111.3 no
H131 . C13 . H133 . 107.1 no
C5 . C14 . O15 . 124.536 yes
C5 . C14 . O16 . 111.579 yes
O15 . C14 . O16 . 123.825 yes
C14 . O16 . C17 . 115.015 yes
O16 . C17 . H172 . 106.7 no
O16 . C17 . H171 . 110.4 no
H172 . C17 . H171 . 113.8 no
O16 . C17 . H173 . 109.4 no
H172 . C17 . H173 . 107.2 no
H171 . C17 . H173 . 109.2 no
C6 . C18 . O19 . 106.934 yes
C6 . C18 . H182 . 110.1 no
O19 . C18 . H182 . 110.4 no
C6 . C18 . H181 . 110.8 no
O19 . C18 . H181 . 108.7 no
H182 . C18 . H181 . 109.8 no
C18 . O19 . C20 . 112.207 yes
O19 . C20 . H201 . 108.1 no
O19 . C20 . H203 . 111.0 no
H201 . C20 . H203 . 108.9 no
O19 . C20 . H202 . 110.5 no
H201 . C20 . H202 . 110.4 no
H203 . C20 . H202 . 107.9 no
C6 . O22 . H221 . 111.0 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C2 0_555 H21 . O19 0_656 145 0.98 2.52 3.366(2) yes
C7 0_555 H71 . O22 0_646 158 0.97 2.41 3.325(2) yes
C13 0_555 H133 . O22 0_555 122 0.97 2.36 2.984(2) yes
O22 0_555 H221 . O3 2_646 170 0.85 1.97 2.812(2) yes
_database_code_depnum_ccdc_archive 'CCDC 952079'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6348
_audit_creation_date             11-09-08
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 6348
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.64000(10)
_cell_length_b                   8.87710(10)
_cell_length_c                   24.8424(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.6556(14)
_cell_angle_gamma                90
_cell_volume                     2101.68(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H26 Br1 N1 O5 
# Dc =      1.39 Fooo =    932.00 Mu =     29.13 M =    880.67
# Found Formula = C20 H27 Br1 N1 O5.50 
# Dc =      1.42 FOOO =    932.00 Mu =     29.43 M =    898.68

_chemical_formula_sum            'C20 H27 Br1 N1 O5.50'
_chemical_formula_moiety         'C20 H26 Br N O5, 0.50(H2 O)'
_chemical_compound_source        .
_chemical_formula_weight         449.34


_cell_measurement_reflns_used    18297
_cell_measurement_theta_min      4
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    2.943

# Sheldrick geometric approximatio 0.56 0.86 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.86
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            37169
_reflns_number_total             8739
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 8739 
# Number of reflections with Friedels Law is 4715 
# Theoretical number of reflections is about 4436 


_diffrn_reflns_theta_min         3.599
_diffrn_reflns_theta_max         76.861
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.861
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   3.40
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.09
_refine_diff_density_max         1.52


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         8739
_refine_ls_number_restraints     1
_refine_ls_number_parameters     497
_oxford_refine_ls_R_factor_ref   0.0439
_refine_ls_wR_factor_ref         0.1029
_refine_ls_goodness_of_fit_ref   0.9968
_refine_ls_shift/su_max          0.0017016
_refine_ls_shift/su_mean         0.0000328


# The values computed from all data 
_oxford_reflns_number_all        8739
_refine_ls_R_factor_all          0.0439
_refine_ls_wR_factor_all         0.1029

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                8333
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.1009

_refine_ls_abs_structure_Flack   -0.028(13)
_refine_ls_abs_structure_details 'Flack (1983), 4024 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 2.49P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.6400 0.0741 0.8878 0.0500 1.0000 Uani . . . . . .
C2 C 0.7176 0.0937 0.8219 0.0337 1.0000 Uani . . . . . .
C3 C 0.6576 0.1936 0.7826 0.0364 1.0000 Uani . . . . . .
C4 C 0.7146 0.2052 0.7347 0.0349 1.0000 Uani . . . . . .
C5 C 0.8274 0.1178 0.7252 0.0318 1.0000 Uani . . . . . .
C6 C 0.8853 0.0179 0.7662 0.0400 1.0000 Uani . . . . . .
C7 C 0.8320 0.0075 0.8146 0.0408 1.0000 Uani . . . . . .
C8 C 0.8853 0.1274 0.6720 0.0378 1.0000 Uani . . . . . .
C9 C 1.0162 0.2254 0.6747 0.0280 1.0000 Uani . . . . . .
O10 O 0.9888 0.3757 0.6900 0.0310 1.0000 Uani . . . . . .
C11 C 1.1461 0.1687 0.7125 0.0326 1.0000 Uani . . . . . .
C12 C 1.2631 0.2543 0.6913 0.0318 1.0000 Uani . . . . . .
O13 O 1.3728 0.2991 0.7173 0.0410 1.0000 Uani . . . . . .
N14 N 1.2229 0.2771 0.6369 0.0267 1.0000 Uani . . . . . .
C15 C 1.0750 0.2386 0.6187 0.0264 1.0000 Uani . . . . . .
C16 C 1.0253 0.3655 0.5776 0.0302 1.0000 Uani . . . . . .
O17 O 1.1285 0.4819 0.5899 0.0330 1.0000 Uani . . . . . .
C18 C 1.2607 0.4124 0.6091 0.0299 1.0000 Uani . . . . . .
C19 C 1.3553 0.3837 0.5652 0.0360 1.0000 Uani . . . . . .
C20 C 1.2951 0.2662 0.5231 0.0403 1.0000 Uani . . . . . .
C21 C 1.4961 0.3281 0.5950 0.0485 1.0000 Uani . . . . . .
C22 C 1.3745 0.5324 0.5364 0.0510 1.0000 Uani . . . . . .
C23 C 0.8807 0.4317 0.5749 0.0419 1.0000 Uani . . . . . .
C24 C 1.0566 0.0866 0.5893 0.0336 1.0000 Uani . . . . . .
O25 O 1.1555 -0.0130 0.6096 0.0445 1.0000 Uani . . . . . .
C26 C 1.1451 -0.1610 0.5847 0.0660 1.0000 Uani . . . . . .
O27 O 0.9651 0.0596 0.5526 0.0482 1.0000 Uani . . . . . .
Br101 Br 0.6787 0.7933 0.6206 0.0750 1.0000 Uani . . . . . .
C102 C 0.5993 0.7667 0.6855 0.0501 1.0000 Uani . . . . . .
C103 C 0.5129 0.8759 0.7017 0.0475 1.0000 Uani . . . . . .
C104 C 0.4603 0.8559 0.7503 0.0403 1.0000 Uani . . . . . .
C105 C 0.4917 0.7286 0.7817 0.0322 1.0000 Uani . . . . . .
C106 C 0.5789 0.6201 0.7641 0.0472 1.0000 Uani . . . . . .
C107 C 0.6351 0.6398 0.7165 0.0561 1.0000 Uani . . . . . .
C108 C 0.4368 0.7098 0.8349 0.0316 1.0000 Uani . . . . . .
C109 C 0.2795 0.6699 0.8289 0.0272 1.0000 Uani . . . . . .
O110 O 0.1970 0.7825 0.7985 0.0308 1.0000 Uani . . . . . .
C111 C 0.2380 0.5157 0.8043 0.0277 1.0000 Uani . . . . . .
C112 C 0.0947 0.4945 0.8220 0.0276 1.0000 Uani . . . . . .
O113 O -0.0078 0.4289 0.7975 0.0348 1.0000 Uani . . . . . .
N114 N 0.0970 0.5658 0.8700 0.0241 1.0000 Uani . . . . . .
C115 C 0.2235 0.6567 0.8851 0.0247 1.0000 Uani . . . . . .
C116 C 0.1678 0.7979 0.9125 0.0293 1.0000 Uani . . . . . .
O117 O 0.0177 0.7885 0.8982 0.0314 1.0000 Uani . . . . . .
C118 C -0.0266 0.6379 0.8870 0.0262 1.0000 Uani . . . . . .
C119 C -0.0842 0.5588 0.9340 0.0298 1.0000 Uani . . . . . .
C120 C 0.0253 0.5444 0.9841 0.0381 1.0000 Uani . . . . . .
C121 C -0.1361 0.4040 0.9134 0.0450 1.0000 Uani . . . . . .
C122 C -0.2075 0.6523 0.9475 0.0453 1.0000 Uani . . . . . .
C123 C 0.2170 0.9519 0.8985 0.0431 1.0000 Uani . . . . . .
C124 C 0.3326 0.5776 0.9273 0.0276 1.0000 Uani . . . . . .
O125 O 0.3312 0.4297 0.9226 0.0316 1.0000 Uani . . . . . .
C126 C 0.4308 0.3488 0.9621 0.0399 1.0000 Uani . . . . . .
O127 O 0.4130 0.6477 0.9603 0.0416 1.0000 Uani . . . . . .
O201 O 0.0467 0.6954 0.6969 0.0733 1.0000 Uani . . . . . .
H31 H 0.5802 0.2531 0.7884 0.0445 1.0000 Uiso R . . . . .
H41 H 0.6738 0.2704 0.7076 0.0417 1.0000 Uiso R . . . . .
H61 H 0.9614 -0.0413 0.7613 0.0480 1.0000 Uiso R . . . . .
H71 H 0.8734 -0.0560 0.8421 0.0490 1.0000 Uiso R . . . . .
H82 H 0.9118 0.0273 0.6627 0.0453 1.0000 Uiso R . . . . .
H81 H 0.8136 0.1641 0.6442 0.0453 1.0000 Uiso R . . . . .
H111 H 1.1425 0.1919 0.7506 0.0386 1.0000 Uiso R . . . . .
H112 H 1.1588 0.0597 0.7096 0.0389 1.0000 Uiso R . . . . .
H161 H 1.0327 0.3264 0.5411 0.0357 1.0000 Uiso R . . . . .
H181 H 1.3134 0.4772 0.6377 0.0354 1.0000 Uiso R . . . . .
H203 H 1.3655 0.2451 0.5004 0.0601 1.0000 Uiso R . . . . .
H202 H 1.2737 0.1749 0.5412 0.0594 1.0000 Uiso R . . . . .
H201 H 1.2114 0.3054 0.5011 0.0596 1.0000 Uiso R . . . . .
H212 H 1.5625 0.3116 0.5704 0.0730 1.0000 Uiso R . . . . .
H213 H 1.5400 0.4015 0.6213 0.0726 1.0000 Uiso R . . . . .
H211 H 1.4866 0.2354 0.6134 0.0729 1.0000 Uiso R . . . . .
H221 H 1.4415 0.5178 0.5118 0.0758 1.0000 Uiso R . . . . .
H223 H 1.4093 0.6057 0.5634 0.0759 1.0000 Uiso R . . . . .
H222 H 1.2873 0.5685 0.5159 0.0755 1.0000 Uiso R . . . . .
H231 H 0.8685 0.5022 0.5458 0.0631 1.0000 Uiso R . . . . .
H233 H 0.8693 0.4786 0.6083 0.0625 1.0000 Uiso R . . . . .
H232 H 0.8137 0.3532 0.5673 0.0627 1.0000 Uiso R . . . . .
H261 H 1.2162 -0.2233 0.6049 0.0988 1.0000 Uiso R . . . . .
H263 H 1.0542 -0.2020 0.5854 0.0991 1.0000 Uiso R . . . . .
H262 H 1.1628 -0.1527 0.5482 0.0990 1.0000 Uiso R . . . . .
H1031 H 0.4909 0.9615 0.6812 0.0577 1.0000 Uiso R . . . . .
H1041 H 0.4050 0.9309 0.7623 0.0483 1.0000 Uiso R . . . . .
H1061 H 0.6002 0.5320 0.7840 0.0566 1.0000 Uiso R . . . . .
H1071 H 0.6958 0.5666 0.7054 0.0670 1.0000 Uiso R . . . . .
H1082 H 0.4523 0.8027 0.8552 0.0373 1.0000 Uiso R . . . . .
H1081 H 0.4910 0.6293 0.8555 0.0375 1.0000 Uiso R . . . . .
H1112 H 0.3020 0.4394 0.8193 0.0323 1.0000 Uiso R . . . . .
H1111 H 0.2309 0.5166 0.7654 0.0318 1.0000 Uiso R . . . . .
H1161 H 0.1877 0.7852 0.9517 0.0344 1.0000 Uiso R . . . . .
H1181 H -0.0976 0.6369 0.8563 0.0306 1.0000 Uiso R . . . . .
H1203 H -0.0148 0.4941 1.0118 0.0566 1.0000 Uiso R . . . . .
H1201 H 0.0556 0.6430 0.9975 0.0568 1.0000 Uiso R . . . . .
H1202 H 0.1039 0.4862 0.9758 0.0569 1.0000 Uiso R . . . . .
H1212 H -0.1794 0.3538 0.9410 0.0673 1.0000 Uiso R . . . . .
H1211 H -0.0580 0.3431 0.9063 0.0666 1.0000 Uiso R . . . . .
H1213 H -0.2016 0.4100 0.8804 0.0667 1.0000 Uiso R . . . . .
H1223 H -0.2492 0.6036 0.9763 0.0677 1.0000 Uiso R . . . . .
H1222 H -0.1749 0.7522 0.9594 0.0677 1.0000 Uiso R . . . . .
H1221 H -0.2771 0.6619 0.9160 0.0683 1.0000 Uiso R . . . . .
H1233 H 0.1745 1.0263 0.9193 0.0651 1.0000 Uiso R . . . . .
H1232 H 0.3180 0.9578 0.9082 0.0649 1.0000 Uiso R . . . . .
H1231 H 0.1926 0.9700 0.8602 0.0645 1.0000 Uiso R . . . . .
H1263 H 0.4145 0.2432 0.9555 0.0601 1.0000 Uiso R . . . . .
H1262 H 0.4128 0.3728 0.9980 0.0598 1.0000 Uiso R . . . . .
H1261 H 0.5256 0.3760 0.9577 0.0597 1.0000 Uiso R . . . . .
H101 H 0.9840 0.3766 0.7230 0.0449 1.0000 Uiso R . . . . .
H1101 H 0.1673 0.7421 0.7697 0.0455 1.0000 Uiso R . . . . .
H2011 H 0.0136 0.6211 0.6793 0.1101 1.0000 Uiso R . . . . .
H2012 H 0.1285 0.6850 0.6906 0.1102 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.449
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.906 yes
C2 . C3 . 1.380 yes
C2 . C7 . 1.377 yes
C3 . C4 . 1.387 yes
C3 . H31 . 0.943 no
C4 . C5 . 1.385 yes
C4 . H41 . 0.931 no
C5 . C6 . 1.401 yes
C5 . C8 . 1.513 yes
C6 . C7 . 1.379 yes
C6 . H61 . 0.925 no
C7 . H71 . 0.929 no
C8 . C9 . 1.526 yes
C8 . H82 . 0.963 no
C8 . H81 . 0.957 no
C9 . O10 . 1.422 yes
C9 . C11 . 1.533 yes
C9 . C15 . 1.584 yes
O10 . H101 . 0.829 no
C11 . C12 . 1.518 yes
C11 . H111 . 0.974 no
C11 . H112 . 0.980 no
C12 . O13 . 1.220 yes
C12 . N14 . 1.363 yes
N14 . C15 . 1.470 yes
N14 . C18 . 1.458 yes
C15 . C16 . 1.547 yes
C15 . C24 . 1.532 yes
C16 . O17 . 1.435 yes
C16 . C23 . 1.505 yes
C16 . H161 . 0.984 no
O17 . C18 . 1.431 yes
C18 . C19 . 1.545 yes
C18 . H181 . 0.991 no
C19 . C20 . 1.528 yes
C19 . C21 . 1.528 yes
C19 . C22 . 1.525 yes
C20 . H203 . 0.965 no
C20 . H202 . 0.963 no
C20 . H201 . 0.968 no
C21 . H212 . 0.961 no
C21 . H213 . 0.973 no
C21 . H211 . 0.953 no
C22 . H221 . 0.962 no
C22 . H223 . 0.959 no
C22 . H222 . 0.969 no
C23 . H231 . 0.948 no
C23 . H233 . 0.950 no
C23 . H232 . 0.950 no
C24 . O25 . 1.341 yes
C24 . O27 . 1.192 yes
O25 . C26 . 1.449 yes
C26 . H261 . 0.961 no
C26 . H263 . 0.951 no
C26 . H262 . 0.950 no
Br101 . C102 . 1.900 yes
C102 . C103 . 1.377 yes
C102 . C107 . 1.378 yes
C103 . C104 . 1.391 yes
C103 . H1031 . 0.921 no
C104 . C105 . 1.380 yes
C104 . H1041 . 0.929 no
C105 . C106 . 1.391 yes
C105 . C108 . 1.506 yes
C106 . C107 . 1.384 yes
C106 . H1061 . 0.933 no
C107 . H1071 . 0.943 no
C108 . C109 . 1.543 yes
C108 . H1082 . 0.966 no
C108 . H1081 . 0.982 no
C109 . O110 . 1.421 yes
C109 . C111 . 1.527 yes
C109 . C115 . 1.577 yes
O110 . H1101 . 0.815 no
C111 . C112 . 1.523 yes
C111 . H1112 . 0.953 no
C111 . H1111 . 0.959 no
C112 . O113 . 1.227 yes
C112 . N114 . 1.347 yes
N114 . C115 . 1.463 yes
N114 . C118 . 1.470 yes
C115 . C116 . 1.559 yes
C115 . C124 . 1.538 yes
C116 . O117 . 1.439 yes
C116 . C123 . 1.505 yes
C116 . H1161 . 0.969 no
O117 . C118 . 1.418 yes
C118 . C119 . 1.535 yes
C118 . H1181 . 0.945 no
C119 . C120 . 1.512 yes
C119 . C121 . 1.524 yes
C119 . C122 . 1.528 yes
C120 . H1203 . 0.950 no
C120 . H1201 . 0.965 no
C120 . H1202 . 0.965 no
C121 . H1212 . 0.963 no
C121 . H1211 . 0.965 no
C121 . H1213 . 0.957 no
C122 . H1223 . 0.973 no
C122 . H1222 . 0.972 no
C122 . H1221 . 0.955 no
C123 . H1233 . 0.966 no
C123 . H1232 . 0.969 no
C123 . H1231 . 0.960 no
C124 . O125 . 1.318 yes
C124 . O127 . 1.211 yes
O125 . C126 . 1.456 yes
C126 . H1263 . 0.960 no
C126 . H1262 . 0.958 no
C126 . H1261 . 0.967 no
O201 . H2011 . 0.829 no
O201 . H2012 . 0.832 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C2 . C3 . 119.289 yes
Br1 . C2 . C7 . 119.255 yes
C3 . C2 . C7 . 121.455 yes
C2 . C3 . C4 . 118.484 yes
C2 . C3 . H31 . 120.6 no
C4 . C3 . H31 . 120.9 no
C3 . C4 . C5 . 121.804 yes
C3 . C4 . H41 . 119.3 no
C5 . C4 . H41 . 118.8 no
C4 . C5 . C6 . 117.894 yes
C4 . C5 . C8 . 121.306 yes
C6 . C5 . C8 . 120.792 yes
C5 . C6 . C7 . 121.044 yes
C5 . C6 . H61 . 120.0 no
C7 . C6 . H61 . 119.0 no
C6 . C7 . C2 . 119.280 yes
C6 . C7 . H71 . 120.5 no
C2 . C7 . H71 . 120.2 no
C5 . C8 . C9 . 113.880 yes
C5 . C8 . H82 . 107.7 no
C9 . C8 . H82 . 106.8 no
C5 . C8 . H81 . 109.2 no
C9 . C8 . H81 . 109.9 no
H82 . C8 . H81 . 109.2 no
C8 . C9 . O10 . 111.174 yes
C8 . C9 . C11 . 115.703 yes
O10 . C9 . C11 . 108.190 yes
C8 . C9 . C15 . 113.966 yes
O10 . C9 . C15 . 105.687 yes
C11 . C9 . C15 . 101.231 yes
C9 . O10 . H101 . 108.2 no
C9 . C11 . C12 . 101.769 yes
C9 . C11 . H111 . 112.3 no
C12 . C11 . H111 . 111.7 no
C9 . C11 . H112 . 112.2 no
C12 . C11 . H112 . 111.2 no
H111 . C11 . H112 . 107.7 no
C11 . C12 . O13 . 127.524 yes
C11 . C12 . N14 . 107.668 yes
O13 . C12 . N14 . 124.788 yes
C12 . N14 . C15 . 112.830 yes
C12 . N14 . C18 . 122.495 yes
C15 . N14 . C18 . 110.246 yes
C9 . C15 . N14 . 101.869 yes
C9 . C15 . C16 . 121.130 yes
N14 . C15 . C16 . 102.894 yes
C9 . C15 . C24 . 108.871 yes
N14 . C15 . C24 . 112.885 yes
C16 . C15 . C24 . 108.938 yes
C15 . C16 . O17 . 104.374 yes
C15 . C16 . C23 . 120.489 yes
O17 . C16 . C23 . 109.645 yes
C15 . C16 . H161 . 107.1 no
O17 . C16 . H161 . 107.7 no
C23 . C16 . H161 . 106.9 no
C16 . O17 . C18 . 108.337 yes
N14 . C18 . O17 . 103.876 yes
N14 . C18 . C19 . 114.500 yes
O17 . C18 . C19 . 115.138 yes
N14 . C18 . H181 . 106.1 no
O17 . C18 . H181 . 108.9 no
C19 . C18 . H181 . 107.9 no
C18 . C19 . C20 . 113.064 yes
C18 . C19 . C21 . 106.596 yes
C20 . C19 . C21 . 109.261 yes
C18 . C19 . C22 . 108.367 yes
C20 . C19 . C22 . 109.300 yes
C21 . C19 . C22 . 110.213 yes
C19 . C20 . H203 . 107.7 no
C19 . C20 . H202 . 110.0 no
H203 . C20 . H202 . 109.2 no
C19 . C20 . H201 . 109.8 no
H203 . C20 . H201 . 109.8 no
H202 . C20 . H201 . 110.3 no
C19 . C21 . H212 . 111.6 no
C19 . C21 . H213 . 112.0 no
H212 . C21 . H213 . 105.5 no
C19 . C21 . H211 . 111.7 no
H212 . C21 . H211 . 107.1 no
H213 . C21 . H211 . 108.7 no
C19 . C22 . H221 . 108.8 no
C19 . C22 . H223 . 108.2 no
H221 . C22 . H223 . 109.7 no
C19 . C22 . H222 . 112.0 no
H221 . C22 . H222 . 108.9 no
H223 . C22 . H222 . 109.1 no
C16 . C23 . H231 . 107.5 no
C16 . C23 . H233 . 111.1 no
H231 . C23 . H233 . 111.0 no
C16 . C23 . H232 . 108.7 no
H231 . C23 . H232 . 109.3 no
H233 . C23 . H232 . 109.3 no
C15 . C24 . O25 . 112.089 yes
C15 . C24 . O27 . 124.073 yes
O25 . C24 . O27 . 123.838 yes
C24 . O25 . C26 . 115.930 yes
O25 . C26 . H261 . 107.5 no
O25 . C26 . H263 . 110.1 no
H261 . C26 . H263 . 110.9 no
O25 . C26 . H262 . 109.0 no
H261 . C26 . H262 . 109.0 no
H263 . C26 . H262 . 110.2 no
Br101 . C102 . C103 . 119.870 yes
Br101 . C102 . C107 . 118.408 yes
C103 . C102 . C107 . 121.674 yes
C102 . C103 . C104 . 118.611 yes
C102 . C103 . H1031 . 121.2 no
C104 . C103 . H1031 . 120.1 no
C103 . C104 . C105 . 121.156 yes
C103 . C104 . H1041 . 119.2 no
C105 . C104 . H1041 . 119.6 no
C104 . C105 . C106 . 118.733 yes
C104 . C105 . C108 . 120.685 yes
C106 . C105 . C108 . 120.546 yes
C105 . C106 . C107 . 120.950 yes
C105 . C106 . H1061 . 120.6 no
C107 . C106 . H1061 . 118.5 no
C106 . C107 . C102 . 118.837 yes
C106 . C107 . H1071 . 120.1 no
C102 . C107 . H1071 . 121.1 no
C105 . C108 . C109 . 114.196 yes
C105 . C108 . H1082 . 108.4 no
C109 . C108 . H1082 . 108.6 no
C105 . C108 . H1081 . 107.9 no
C109 . C108 . H1081 . 108.8 no
H1082 . C108 . H1081 . 108.8 no
C108 . C109 . O110 . 110.729 yes
C108 . C109 . C111 . 116.047 yes
O110 . C109 . C111 . 109.066 yes
C108 . C109 . C115 . 113.184 yes
O110 . C109 . C115 . 106.468 yes
C111 . C109 . C115 . 100.548 yes
C109 . O110 . H1101 . 104.6 no
C109 . C111 . C112 . 100.966 yes
C109 . C111 . H1112 . 111.5 no
C112 . C111 . H1112 . 111.3 no
C109 . C111 . H1111 . 111.7 no
C112 . C111 . H1111 . 111.2 no
H1112 . C111 . H1111 . 110.0 no
C111 . C112 . O113 . 127.832 yes
C111 . C112 . N114 . 107.557 yes
O113 . C112 . N114 . 124.583 yes
C112 . N114 . C115 . 112.927 yes
C112 . N114 . C118 . 123.611 yes
C115 . N114 . C118 . 111.476 yes
C109 . C115 . N114 . 101.297 yes
C109 . C115 . C116 . 120.872 yes
N114 . C115 . C116 . 103.148 yes
C109 . C115 . C124 . 110.316 yes
N114 . C115 . C124 . 112.477 yes
C116 . C115 . C124 . 108.336 yes
C115 . C116 . O117 . 104.157 yes
C115 . C116 . C123 . 119.234 yes
O117 . C116 . C123 . 109.588 yes
C115 . C116 . H1161 . 108.4 no
O117 . C116 . H1161 . 106.3 no
C123 . C116 . H1161 . 108.4 no
C116 . O117 . C118 . 111.419 yes
N114 . C118 . O117 . 103.464 yes
N114 . C118 . C119 . 114.929 yes
O117 . C118 . C119 . 114.546 yes
N114 . C118 . H1181 . 106.4 no
O117 . C118 . H1181 . 109.1 no
C119 . C118 . H1181 . 108.0 no
C118 . C119 . C120 . 112.162 yes
C118 . C119 . C121 . 107.206 yes
C120 . C119 . C121 . 110.681 yes
C118 . C119 . C122 . 107.488 yes
C120 . C119 . C122 . 109.561 yes
C121 . C119 . C122 . 109.653 yes
C119 . C120 . H1203 . 109.1 no
C119 . C120 . H1201 . 110.1 no
H1203 . C120 . H1201 . 108.2 no
C119 . C120 . H1202 . 110.0 no
H1203 . C120 . H1202 . 108.8 no
H1201 . C120 . H1202 . 110.7 no
C119 . C121 . H1212 . 109.6 no
C119 . C121 . H1211 . 110.0 no
H1212 . C121 . H1211 . 107.7 no
C119 . C121 . H1213 . 112.2 no
H1212 . C121 . H1213 . 109.5 no
H1211 . C121 . H1213 . 107.9 no
C119 . C122 . H1223 . 110.0 no
C119 . C122 . H1222 . 109.6 no
H1223 . C122 . H1222 . 109.4 no
C119 . C122 . H1221 . 110.0 no
H1223 . C122 . H1221 . 109.0 no
H1222 . C122 . H1221 . 108.9 no
C116 . C123 . H1233 . 108.9 no
C116 . C123 . H1232 . 109.3 no
H1233 . C123 . H1232 . 108.8 no
C116 . C123 . H1231 . 110.0 no
H1233 . C123 . H1231 . 110.8 no
H1232 . C123 . H1231 . 109.0 no
C115 . C124 . O125 . 113.377 yes
C115 . C124 . O127 . 121.944 yes
O125 . C124 . O127 . 124.656 yes
C124 . O125 . C126 . 115.740 yes
O125 . C126 . H1263 . 107.0 no
O125 . C126 . H1262 . 108.9 no
H1263 . C126 . H1262 . 109.1 no
O125 . C126 . H1261 . 109.8 no
H1263 . C126 . H1261 . 111.0 no
H1262 . C126 . H1261 . 110.9 no
H2011 . O201 . H2012 . 96.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 0_555 H31 . O13 0_455 124 0.94 2.49 3.116(5) yes
C7 0_555 H71 . O117 0_645 166 0.93 2.28 3.191(5) yes
C123 0_555 H1231 . O110 . 121 0.96 2.27 2.885(5) yes
O10 0_555 H101 . O113 . 165 0.83 1.90 2.707(5) yes
O110 0_555 H1101 . O201 0_555 161 0.81 2.04 2.823(5) yes
O201 0_555 H2011 . O10 1_455 140 0.83 2.21 2.892(5) yes
_database_code_depnum_ccdc_archive 'CCDC 952080'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6297
_audit_creation_date             11-02-14
_audit_creation_method           CRYSTALS_ver_14.18

_oxford_structure_analysis_title 6297
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   8.9582(1)
_cell_length_b                   10.6774(1)
_cell_length_c                   9.5609(1)
_cell_angle_alpha                90
_cell_angle_beta                 112.3017(15)
_cell_angle_gamma                90
_cell_volume                     846.097(18)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C16 H27 N1 O6 
# Dc =      1.29 Fooo =    356.00 Mu =      8.16 M =    329.39
# Found Formula = C16 H27 N1 O6 
# Dc =      1.29 FOOO =    356.00 Mu =      8.16 M =    329.39

_chemical_formula_sum            'C16 H27 N1 O6'
_chemical_formula_moiety         'C16 H27 N1 O6'
_chemical_compound_source        .
_chemical_formula_weight         329.39


_cell_measurement_reflns_used    14137
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.816

# Sheldrick geometric approximatio 0.91 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd. (Oxford Diffraction, 2002),
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            18654
_reflns_number_total             3509
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 3509 
# Number of reflections with Friedels Law is 1862 
# Theoretical number of reflections is about 1774 


_diffrn_reflns_theta_min         5.000
_diffrn_reflns_theta_max         76.326
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.326
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.18


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     1
_refine_ls_number_parameters     210
_oxford_refine_ls_R_factor_ref   0.0240
_refine_ls_wR_factor_ref         0.0610
_refine_ls_goodness_of_fit_ref   1.0058
_refine_ls_shift/su_max          0.0003091
_refine_ls_shift/su_mean         0.0000285


# The values computed from all data 
_oxford_reflns_number_all        3509
_refine_ls_R_factor_all          0.0240
_refine_ls_wR_factor_all         0.0610

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3437
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_gt          0.0601

_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_abs_structure_details 'Flack (1983), 1647 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.10P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.3987 0.7177 -0.0856 0.0192 1.0000 Uani . . . . . .
C2 C 0.2929 0.8085 -0.1925 0.0204 1.0000 Uani . . . . . .
O3 O 0.2341 0.8839 -0.1003 0.0225 1.0000 Uani . . . . . .
C4 C 0.2320 0.8106 0.0252 0.0213 1.0000 Uani . . . . . .
C5 C 0.3740 0.7162 0.0571 0.0191 1.0000 Uani . . . . . .
C6 C 0.5487 0.7461 0.1773 0.0209 1.0000 Uani . . . . . .
C7 C 0.6522 0.6787 0.1029 0.0226 1.0000 Uani . . . . . .
C8 C 0.5595 0.7052 -0.0641 0.0206 1.0000 Uani . . . . . .
C9 C 0.1587 0.7524 -0.3323 0.0248 1.0000 Uani . . . . . .
C10 C 0.2404 0.6735 -0.4169 0.0323 1.0000 Uani . . . . . .
C11 C 0.0691 0.8622 -0.4318 0.0308 1.0000 Uani . . . . . .
C12 C 0.0401 0.6696 -0.2937 0.0346 1.0000 Uani . . . . . .
C13 C 0.2303 0.8980 0.1497 0.0273 1.0000 Uani . . . . . .
C14 C 0.3205 0.5855 0.0848 0.0218 1.0000 Uani . . . . . .
O15 O 0.3427 0.4907 0.0283 0.0306 1.0000 Uani . . . . . .
O16 O 0.2430 0.5905 0.1794 0.0270 1.0000 Uani . . . . . .
C17 C 0.1940 0.4705 0.2191 0.0353 1.0000 Uani . . . . . .
O18 O 0.5765 0.8765 0.1911 0.0247 1.0000 Uani . . . . . .
C19 C 0.5809 0.7051 0.3387 0.0255 1.0000 Uani . . . . . .
O20 O 0.5847 0.5731 0.3491 0.0291 1.0000 Uani . . . . . .
C21 C 0.5842 0.5326 0.4908 0.0360 1.0000 Uani . . . . . .
C22 C 0.8299 0.7137 0.1579 0.0310 1.0000 Uani . . . . . .
O23 O 0.6124 0.7158 -0.1628 0.0253 1.0000 Uani . . . . . .
H133 H 0.2253 0.8482 0.2340 0.0404 1.0000 Uiso R . . . . .
H132 H 0.3230 0.9498 0.1851 0.0398 1.0000 Uiso R . . . . .
H131 H 0.1335 0.9488 0.1094 0.0393 1.0000 Uiso R . . . . .
H41 H 0.1326 0.7593 -0.0064 0.0232 1.0000 Uiso R . . . . .
H113 H -0.0188 0.8321 -0.5192 0.0462 1.0000 Uiso R . . . . .
H111 H 0.1423 0.9091 -0.4655 0.0465 1.0000 Uiso R . . . . .
H112 H 0.0266 0.9179 -0.3771 0.0471 1.0000 Uiso R . . . . .
H122 H -0.0323 0.6312 -0.3858 0.0515 1.0000 Uiso R . . . . .
H121 H -0.0243 0.7198 -0.2504 0.0497 1.0000 Uiso R . . . . .
H123 H 0.0951 0.6031 -0.2254 0.0498 1.0000 Uiso R . . . . .
H103 H 0.1613 0.6482 -0.5149 0.0470 1.0000 Uiso R . . . . .
H101 H 0.3228 0.7207 -0.4349 0.0477 1.0000 Uiso R . . . . .
H102 H 0.2897 0.5997 -0.3589 0.0474 1.0000 Uiso R . . . . .
H21 H 0.3628 0.8652 -0.2264 0.0223 1.0000 Uiso R . . . . .
H223 H 0.8852 0.6839 0.2632 0.0460 1.0000 Uiso R . . . . .
H222 H 0.8447 0.8039 0.1575 0.0441 1.0000 Uiso R . . . . .
H221 H 0.8796 0.6724 0.0967 0.0445 1.0000 Uiso R . . . . .
H71 H 0.6439 0.5917 0.1162 0.0268 1.0000 Uiso R . . . . .
H172 H 0.1805 0.4792 0.3142 0.0570 1.0000 Uiso R . . . . .
H171 H 0.2750 0.4120 0.2316 0.0537 1.0000 Uiso R . . . . .
H173 H 0.0967 0.4471 0.1477 0.0568 1.0000 Uiso R . . . . .
H212 H 0.5896 0.4437 0.4952 0.0530 1.0000 Uiso R . . . . .
H211 H 0.6763 0.5651 0.5746 0.0523 1.0000 Uiso R . . . . .
H213 H 0.4859 0.5566 0.4994 0.0529 1.0000 Uiso R . . . . .
H192 H 0.6859 0.7420 0.4095 0.0309 1.0000 Uiso R . . . . .
H191 H 0.4961 0.7386 0.3714 0.0293 1.0000 Uiso R . . . . .
H181 H 0.5906 0.9056 0.1162 0.0370 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       44.355
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          13.525
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.465 yes
N1 . C5 . 1.462 yes
N1 . C8 . 1.382 yes
C2 . O3 . 1.433 yes
C2 . C9 . 1.540 yes
C2 . H21 . 1.009 no
O3 . C4 . 1.438 yes
C4 . C5 . 1.560 yes
C4 . C13 . 1.516 yes
C4 . H41 . 0.991 no
C5 . C6 . 1.583 yes
C5 . C14 . 1.531 yes
C6 . C7 . 1.544 yes
C6 . C19 . 1.522 yes
C6 . O18 . 1.412 yes
C7 . C8 . 1.521 yes
C7 . C22 . 1.521 yes
C7 . H71 . 0.944 no
C8 . O23 . 1.211 yes
C9 . C10 . 1.533 yes
C9 . C11 . 1.531 yes
C9 . C12 . 1.531 yes
C10 . H103 . 0.974 no
C10 . H101 . 0.962 no
C10 . H102 . 0.968 no
C11 . H113 . 0.960 no
C11 . H111 . 0.972 no
C11 . H112 . 0.961 no
C12 . H122 . 0.965 no
C12 . H121 . 0.986 no
C12 . H123 . 0.964 no
C13 . H133 . 0.981 no
C13 . H132 . 0.946 no
C13 . H131 . 0.970 no
C14 . O15 . 1.199 yes
C14 . O16 . 1.334 yes
O16 . C17 . 1.451 yes
C17 . H172 . 0.966 no
C17 . H171 . 0.930 no
C17 . H173 . 0.914 no
O18 . H181 . 0.833 no
C19 . O20 . 1.413 yes
C19 . H192 . 1.007 no
C19 . H191 . 0.991 no
O20 . C21 . 1.424 yes
C21 . H212 . 0.951 no
C21 . H211 . 0.970 no
C21 . H213 . 0.950 no
C22 . H223 . 0.990 no
C22 . H222 . 0.973 no
C22 . H221 . 0.967 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 111.759 yes
C2 . N1 . C8 . 121.993 yes
C5 . N1 . C8 . 112.248 yes
N1 . C2 . O3 . 103.519 yes
N1 . C2 . C9 . 115.706 yes
O3 . C2 . C9 . 113.879 yes
N1 . C2 . H21 . 107.7 no
O3 . C2 . H21 . 106.2 no
C9 . C2 . H21 . 109.3 no
C2 . O3 . C4 . 109.395 yes
O3 . C4 . C5 . 104.254 yes
O3 . C4 . C13 . 109.102 yes
C5 . C4 . C13 . 119.657 yes
O3 . C4 . H41 . 109.9 no
C5 . C4 . H41 . 105.9 no
C13 . C4 . H41 . 107.7 no
C4 . C5 . N1 . 102.230 yes
C4 . C5 . C6 . 121.305 yes
N1 . C5 . C6 . 102.544 yes
C4 . C5 . C14 . 109.723 yes
N1 . C5 . C14 . 109.868 yes
C6 . C5 . C14 . 110.217 yes
C5 . C6 . C7 . 99.929 yes
C5 . C6 . C19 . 115.677 yes
C7 . C6 . C19 . 114.651 yes
C5 . C6 . O18 . 110.933 yes
C7 . C6 . O18 . 112.759 yes
C19 . C6 . O18 . 103.284 yes
C6 . C7 . C8 . 102.302 yes
C6 . C7 . C22 . 117.283 yes
C8 . C7 . C22 . 113.595 yes
C6 . C7 . H71 . 107.7 no
C8 . C7 . H71 . 106.6 no
C22 . C7 . H71 . 108.7 no
C7 . C8 . N1 . 107.266 yes
C7 . C8 . O23 . 128.039 yes
N1 . C8 . O23 . 124.687 yes
C2 . C9 . C10 . 107.469 yes
C2 . C9 . C11 . 107.095 yes
C10 . C9 . C11 . 109.632 yes
C2 . C9 . C12 . 113.557 yes
C10 . C9 . C12 . 108.905 yes
C11 . C9 . C12 . 110.099 yes
C9 . C10 . H103 . 109.9 no
C9 . C10 . H101 . 111.0 no
H103 . C10 . H101 . 107.5 no
C9 . C10 . H102 . 110.5 no
H103 . C10 . H102 . 109.5 no
H101 . C10 . H102 . 108.3 no
C9 . C11 . H113 . 110.4 no
C9 . C11 . H111 . 109.9 no
H113 . C11 . H111 . 108.5 no
C9 . C11 . H112 . 111.0 no
H113 . C11 . H112 . 108.5 no
H111 . C11 . H112 . 108.6 no
C9 . C12 . H122 . 108.2 no
C9 . C12 . H121 . 110.9 no
H122 . C12 . H121 . 108.5 no
C9 . C12 . H123 . 111.4 no
H122 . C12 . H123 . 107.4 no
H121 . C12 . H123 . 110.3 no
C4 . C13 . H133 . 109.2 no
C4 . C13 . H132 . 111.8 no
H133 . C13 . H132 . 109.3 no
C4 . C13 . H131 . 107.8 no
H133 . C13 . H131 . 108.4 no
H132 . C13 . H131 . 110.3 no
C5 . C14 . O15 . 125.113 yes
C5 . C14 . O16 . 111.038 yes
O15 . C14 . O16 . 123.841 yes
C14 . O16 . C17 . 115.440 yes
O16 . C17 . H172 . 108.6 no
O16 . C17 . H171 . 109.1 no
H172 . C17 . H171 . 108.3 no
O16 . C17 . H173 . 110.0 no
H172 . C17 . H173 . 107.8 no
H171 . C17 . H173 . 112.9 no
C6 . O18 . H181 . 111.5 no
C6 . C19 . O20 . 110.378 yes
C6 . C19 . H192 . 109.8 no
O20 . C19 . H192 . 110.6 no
C6 . C19 . H191 . 110.1 no
O20 . C19 . H191 . 109.8 no
H192 . C19 . H191 . 106.2 no
C19 . O20 . C21 . 111.142 yes
O20 . C21 . H212 . 109.1 no
O20 . C21 . H211 . 111.6 no
H212 . C21 . H211 . 107.9 no
O20 . C21 . H213 . 109.8 no
H212 . C21 . H213 . 107.4 no
H211 . C21 . H213 . 110.9 no
C7 . C22 . H223 . 109.1 no
C7 . C22 . H222 . 111.6 no
H223 . C22 . H222 . 107.8 no
C7 . C22 . H221 . 109.9 no
H223 . C22 . H221 . 107.6 no
H222 . C22 . H221 . 110.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 0_555 H132 . O18 0_555 121 0.95 2.38 2.9824(18) yes
C7 0_555 H71 . O3 2_645 144 0.94 2.50 3.3115(18) yes
C17 0_555 H171 . O23 0_645 154 0.93 2.52 3.3764(18) yes
O18 0_555 H181 . O15 . 169 0.83 1.93 2.7500(18) yes
_database_code_depnum_ccdc_archive 'CCDC 952081'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6349
_audit_creation_date             11-09-04
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 6349
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.9357(2)
_cell_length_b                   9.2334(2)
_cell_length_c                   11.0082(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.2517(15)
_cell_angle_gamma                90
_cell_volume                     1090.17(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C21 H28 Br1 N1 O5 
# Dc =      1.38 Fooo =    472.00 Mu =     28.25 M =    454.36
# Found Formula = C21 H28 Br1 N1 O5 
# Dc =      1.38 FOOO =    472.00 Mu =     28.25 M =    454.36

_chemical_formula_sum            'C21 H28 Br1 N1 O5'
_chemical_formula_moiety         'C21 H28 Br1 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         454.36


_cell_measurement_reflns_used    10789
_cell_measurement_theta_min      4
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.010
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_max          0.210

_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    2.825

# Sheldrick geometric approximatio 0.78 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            17112
_reflns_number_total             4317
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 4317 
# Number of reflections with Friedels Law is 2423 
# Theoretical number of reflections is about 2299 


_diffrn_reflns_theta_min         4.095
_diffrn_reflns_theta_max         76.767
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        75.232
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -11
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.66
_refine_diff_density_max         0.47


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     1
_refine_ls_number_parameters     254
_oxford_refine_ls_R_factor_ref   0.0304
_refine_ls_wR_factor_ref         0.0767
_refine_ls_goodness_of_fit_ref   1.0016
_refine_ls_shift/su_max          0.0015411
_refine_ls_shift/su_mean         0.0000447


# The values computed from all data 
_oxford_reflns_number_all        4317
_refine_ls_R_factor_all          0.0304
_refine_ls_wR_factor_all         0.0767

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4175
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_gt          0.0755

_refine_ls_abs_structure_Flack   -0.012(13)
_refine_ls_abs_structure_details 'Flack (1983), 1894 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.32P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.9892 0.7477 1.5245 0.0739 1.0000 Uani . . . . . .
C2 C 0.9085 0.6710 1.3690 0.0445 1.0000 Uani . . . . . .
C3 C 0.9340 0.7301 1.2615 0.0401 1.0000 Uani . . . . . .
C4 C 0.8733 0.6729 1.1485 0.0323 1.0000 Uani . . . . . .
C5 C 0.7891 0.5589 1.1447 0.0307 1.0000 Uani . . . . . .
C6 C 0.7662 0.5042 1.2551 0.0394 1.0000 Uani . . . . . .
C7 C 0.8263 0.5586 1.3687 0.0466 1.0000 Uani . . . . . .
C8 C 0.7173 0.5011 1.0231 0.0329 1.0000 Uani . . . . . .
C9 C 0.7798 0.3811 0.9600 0.0238 1.0000 Uani . . . . . .
O10 O 0.8864 0.4308 0.9182 0.0259 1.0000 Uani . . . . . .
C11 C 0.6884 0.3209 0.8414 0.0228 1.0000 Uani . . . . . .
N12 N 0.7370 0.1764 0.8269 0.0248 1.0000 Uani . . . . . .
C13 C 0.7554 0.1518 0.7003 0.0278 1.0000 Uani . . . . . .
O14 O 0.7602 0.2940 0.6526 0.0288 1.0000 Uani . . . . . .
C15 C 0.6847 0.3882 0.7102 0.0257 1.0000 Uani . . . . . .
C16 C 0.7264 0.5434 0.7007 0.0356 1.0000 Uani . . . . . .
C17 C 0.6591 0.0513 0.6208 0.0365 1.0000 Uani . . . . . .
C18 C 0.5244 0.1022 0.6094 0.0416 1.0000 Uani . . . . . .
C19 C 0.6733 -0.0959 0.6823 0.0607 1.0000 Uani . . . . . .
C20 C 0.6912 0.0420 0.4923 0.0605 1.0000 Uani . . . . . .
C21 C 0.8176 0.1302 0.9310 0.0262 1.0000 Uani . . . . . .
C22 C 0.8124 0.2379 1.0341 0.0273 1.0000 Uani . . . . . .
C23 C 0.9313 0.2367 1.1328 0.0353 1.0000 Uani . . . . . .
O24 O 0.8826 0.0220 0.9356 0.0352 1.0000 Uani . . . . . .
C25 C 0.5571 0.3102 0.8698 0.0274 1.0000 Uani . . . . . .
O26 O 0.4881 0.4248 0.8244 0.0318 1.0000 Uani . . . . . .
C27 C 0.3638 0.4300 0.8501 0.0475 1.0000 Uani . . . . . .
O28 O 0.5215 0.2134 0.9275 0.0392 1.0000 Uani . . . . . .
H31 H 0.9900 0.8017 1.2612 0.0487 1.0000 Uiso R . . . . .
H41 H 0.8900 0.7118 1.0768 0.0379 1.0000 Uiso R . . . . .
H61 H 0.7096 0.4298 1.2529 0.0468 1.0000 Uiso R . . . . .
H71 H 0.8115 0.5197 1.4422 0.0562 1.0000 Uiso R . . . . .
H82 H 0.6983 0.5831 0.9675 0.0390 1.0000 Uiso R . . . . .
H81 H 0.6368 0.4598 1.0384 0.0392 1.0000 Uiso R . . . . .
H101 H 0.9409 0.4573 0.9754 0.0390 1.0000 Uiso R . . . . .
H131 H 0.8380 0.1052 0.7052 0.0319 1.0000 Uiso R . . . . .
H151 H 0.5983 0.3805 0.6640 0.0298 1.0000 Uiso R . . . . .
H162 H 0.7062 0.5722 0.6138 0.0519 1.0000 Uiso R . . . . .
H161 H 0.8145 0.5553 0.7309 0.0525 1.0000 Uiso R . . . . .
H163 H 0.6816 0.6051 0.7501 0.0518 1.0000 Uiso R . . . . .
H182 H 0.4691 0.0291 0.5668 0.0613 1.0000 Uiso R . . . . .
H181 H 0.5078 0.1146 0.6907 0.0610 1.0000 Uiso R . . . . .
H183 H 0.5107 0.1926 0.5651 0.0625 1.0000 Uiso R . . . . .
H193 H 0.6190 -0.1637 0.6302 0.0910 1.0000 Uiso R . . . . .
H192 H 0.7595 -0.1278 0.6938 0.0907 1.0000 Uiso R . . . . .
H191 H 0.6465 -0.0933 0.7624 0.0890 1.0000 Uiso R . . . . .
H203 H 0.6352 -0.0259 0.4439 0.0907 1.0000 Uiso R . . . . .
H202 H 0.7738 0.0090 0.4977 0.0915 1.0000 Uiso R . . . . .
H201 H 0.6832 0.1384 0.4542 0.0909 1.0000 Uiso R . . . . .
H221 H 0.7426 0.2125 1.0732 0.0331 1.0000 Uiso R . . . . .
H233 H 0.9458 0.1423 1.1701 0.0524 1.0000 Uiso R . . . . .
H232 H 0.9237 0.3043 1.1959 0.0522 1.0000 Uiso R . . . . .
H231 H 1.0016 0.2650 1.0987 0.0527 1.0000 Uiso R . . . . .
H273 H 0.3224 0.5120 0.8064 0.0702 1.0000 Uiso R . . . . .
H272 H 0.3670 0.4347 0.9371 0.0694 1.0000 Uiso R . . . . .
H271 H 0.3223 0.3429 0.8184 0.0711 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.323
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.903 yes
C2 . C3 . 1.380 yes
C2 . C7 . 1.372 yes
C3 . C4 . 1.394 yes
C3 . H31 . 0.902 no
C4 . C5 . 1.394 yes
C4 . H41 . 0.917 no
C5 . C6 . 1.383 yes
C5 . C8 . 1.511 yes
C6 . C7 . 1.388 yes
C6 . H61 . 0.922 no
C7 . H71 . 0.929 no
C8 . C9 . 1.537 yes
C8 . H82 . 0.970 no
C8 . H81 . 1.003 no
C9 . O10 . 1.412 yes
C9 . C11 . 1.582 yes
C9 . C22 . 1.557 yes
O10 . H101 . 0.815 no
C11 . N12 . 1.456 yes
C11 . C15 . 1.566 yes
C11 . C25 . 1.531 yes
N12 . C13 . 1.465 yes
N12 . C21 . 1.370 yes
C13 . O14 . 1.419 yes
C13 . C17 . 1.541 yes
C13 . H131 . 0.992 no
O14 . C15 . 1.429 yes
C15 . C16 . 1.514 yes
C15 . H151 . 0.985 no
C16 . H162 . 0.976 no
C16 . H161 . 0.962 no
C16 . H163 . 0.982 no
C17 . C18 . 1.527 yes
C17 . C19 . 1.513 yes
C17 . C20 . 1.525 yes
C18 . H182 . 0.965 no
C18 . H181 . 0.955 no
C18 . H183 . 0.963 no
C19 . H193 . 0.970 no
C19 . H192 . 0.972 no
C19 . H191 . 0.982 no
C20 . H203 . 0.962 no
C20 . H202 . 0.944 no
C20 . H201 . 0.981 no
C21 . C22 . 1.519 yes
C21 . O24 . 1.221 yes
C22 . C23 . 1.523 yes
C22 . H221 . 0.975 no
C23 . H233 . 0.963 no
C23 . H232 . 0.949 no
C23 . H231 . 0.956 no
C25 . O26 . 1.338 yes
C25 . O28 . 1.204 yes
O26 . C27 . 1.443 yes
C27 . H273 . 0.962 no
C27 . H272 . 0.953 no
C27 . H271 . 0.955 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C2 . C3 . 119.245 yes
Br1 . C2 . C7 . 118.216 yes
C3 . C2 . C7 . 122.538 yes
C2 . C3 . C4 . 118.378 yes
C2 . C3 . H31 . 122.9 no
C4 . C3 . H31 . 118.6 no
C3 . C4 . C5 . 120.569 yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 120.8 no
C4 . C5 . C6 . 118.814 yes
C4 . C5 . C8 . 121.258 yes
C6 . C5 . C8 . 119.816 yes
C5 . C6 . C7 . 121.571 yes
C5 . C6 . H61 . 119.0 no
C7 . C6 . H61 . 119.4 no
C6 . C7 . C2 . 118.122 yes
C6 . C7 . H71 . 120.8 no
C2 . C7 . H71 . 121.0 no
C5 . C8 . C9 . 117.046 yes
C5 . C8 . H82 . 107.1 no
C9 . C8 . H82 . 109.7 no
C5 . C8 . H81 . 107.9 no
C9 . C8 . H81 . 106.5 no
H82 . C8 . H81 . 108.4 no
C8 . C9 . O10 . 112.438 yes
C8 . C9 . C11 . 111.159 yes
O10 . C9 . C11 . 105.920 yes
C8 . C9 . C22 . 116.844 yes
O10 . C9 . C22 . 109.147 yes
C11 . C9 . C22 . 100.174 yes
C9 . O10 . H101 . 111.8 no
C9 . C11 . N12 . 103.147 yes
C9 . C11 . C15 . 121.333 yes
N12 . C11 . C15 . 101.913 yes
C9 . C11 . C25 . 108.747 yes
N12 . C11 . C25 . 109.887 yes
C15 . C11 . C25 . 110.920 yes
C11 . N12 . C13 . 111.579 yes
C11 . N12 . C21 . 112.496 yes
C13 . N12 . C21 . 124.169 yes
N12 . C13 . O14 . 103.278 yes
N12 . C13 . C17 . 115.340 yes
O14 . C13 . C17 . 114.683 yes
N12 . C13 . H131 . 107.9 no
O14 . C13 . H131 . 108.8 no
C17 . C13 . H131 . 106.5 no
C13 . O14 . C15 . 109.474 yes
C11 . C15 . O14 . 104.747 yes
C11 . C15 . C16 . 119.048 yes
O14 . C15 . C16 . 109.752 yes
C11 . C15 . H151 . 107.3 no
O14 . C15 . H151 . 107.9 no
C16 . C15 . H151 . 107.7 no
C15 . C16 . H162 . 108.2 no
C15 . C16 . H161 . 112.3 no
H162 . C16 . H161 . 109.1 no
C15 . C16 . H163 . 108.8 no
H162 . C16 . H163 . 110.0 no
H161 . C16 . H163 . 108.5 no
C13 . C17 . C18 . 113.746 yes
C13 . C17 . C19 . 106.712 yes
C18 . C17 . C19 . 109.088 yes
C13 . C17 . C20 . 107.710 yes
C18 . C17 . C20 . 109.518 yes
C19 . C17 . C20 . 110.001 yes
C17 . C18 . H182 . 109.2 no
C17 . C18 . H181 . 108.5 no
H182 . C18 . H181 . 108.8 no
C17 . C18 . H183 . 111.1 no
H182 . C18 . H183 . 109.9 no
H181 . C18 . H183 . 109.4 no
C17 . C19 . H193 . 108.5 no
C17 . C19 . H192 . 110.0 no
H193 . C19 . H192 . 110.4 no
C17 . C19 . H191 . 110.9 no
H193 . C19 . H191 . 106.9 no
H192 . C19 . H191 . 110.0 no
C17 . C20 . H203 . 108.2 no
C17 . C20 . H202 . 110.6 no
H203 . C20 . H202 . 108.8 no
C17 . C20 . H201 . 109.2 no
H203 . C20 . H201 . 111.2 no
H202 . C20 . H201 . 109.0 no
N12 . C21 . C22 . 107.963 yes
N12 . C21 . O24 . 124.358 yes
C22 . C21 . O24 . 127.666 yes
C9 . C22 . C21 . 101.715 yes
C9 . C22 . C23 . 117.144 yes
C21 . C22 . C23 . 112.135 yes
C9 . C22 . H221 . 108.5 no
C21 . C22 . H221 . 108.6 no
C23 . C22 . H221 . 108.4 no
C22 . C23 . H233 . 111.0 no
C22 . C23 . H232 . 109.5 no
H233 . C23 . H232 . 108.3 no
C22 . C23 . H231 . 111.0 no
H233 . C23 . H231 . 109.6 no
H232 . C23 . H231 . 107.4 no
C11 . C25 . O26 . 110.826 yes
C11 . C25 . O28 . 124.607 yes
O26 . C25 . O28 . 124.546 yes
C25 . O26 . C27 . 115.908 yes
O26 . C27 . H273 . 107.3 no
O26 . C27 . H272 . 110.3 no
H273 . C27 . H272 . 112.8 no
O26 . C27 . H271 . 107.4 no
H273 . C27 . H271 . 109.7 no
H272 . C27 . H271 . 109.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O10 0_555 H101 . O24 0_757 157 0.82 2.07 2.845(3) yes
_database_code_depnum_ccdc_archive 'CCDC 952082'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6345
_audit_creation_date             11-09-05
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 6345
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.0903(1)
_cell_length_b                   9.5673(1)
_cell_length_c                   24.6946(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2147.68(3)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C21 H29 N1 O5 S1 
# Dc =      1.26 Fooo =    872.00 Mu =     15.96 M =    407.53
# Found Formula = C21 H29 N1 O5 S1 
# Dc =      1.26 FOOO =    872.00 Mu =     15.96 M =    407.53

_chemical_formula_sum            'C21 H29 N1 O5 S1'
_chemical_formula_moiety         'C21 H29 N1 O5 S1'
_chemical_compound_source        .
_chemical_formula_weight         407.53

_cell_measurement_reflns_used    36783
_cell_measurement_theta_min      4
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.060
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.220

_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.596

# Sheldrick geometric approximatio 0.84 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            53357
_reflns_number_total             4530
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections without Friedels Law is 4530 
# Number of reflections with Friedels Law is 2599 
# Theoretical number of reflections is about 2268 


_diffrn_reflns_theta_min         3.580
_diffrn_reflns_theta_max         76.913
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        76.913
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   2.62
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.16


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     0
_refine_ls_number_parameters     254
_oxford_refine_ls_R_factor_ref   0.0214
_refine_ls_wR_factor_ref         0.0577
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_shift/su_max          0.0005475
_refine_ls_shift/su_mean         0.0000620


# The values computed from all data 
_oxford_reflns_number_all        4530
_refine_ls_R_factor_all          0.0214
_refine_ls_wR_factor_all         0.0577

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4488
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_gt          0.0575

_refine_ls_abs_structure_Flack   -0.010(9)
_refine_ls_abs_structure_details 'Flack (1983), 1931 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.24P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.8266 0.9058 0.3370 0.0354 1.0000 Uani . . . . . .
C2 C 0.6327 0.8781 0.3223 0.0305 1.0000 Uani . . . . . .
C3 C 0.5729 0.7282 0.3240 0.0251 1.0000 Uani . . . . . .
O4 O 0.4292 0.7278 0.3011 0.0284 1.0000 Uani . . . . . .
C5 C 0.6656 0.6135 0.2958 0.0251 1.0000 Uani . . . . . .
C6 C 0.6705 0.6149 0.2341 0.0306 1.0000 Uani . . . . . .
C7 C 0.5888 0.4850 0.3181 0.0249 1.0000 Uani . . . . . .
O8 O 0.5634 0.3743 0.2951 0.0305 1.0000 Uani . . . . . .
N9 N 0.5433 0.5133 0.3697 0.0245 1.0000 Uani . . . . . .
C10 C 0.5532 0.6628 0.3821 0.0250 1.0000 Uani . . . . . .
C11 C 0.6838 0.6988 0.4188 0.0279 1.0000 Uani . . . . . .
O12 O 0.7946 0.6085 0.4141 0.0325 1.0000 Uani . . . . . .
C13 C 0.9254 0.6411 0.4450 0.0440 1.0000 Uani . . . . . .
O14 O 0.6831 0.7986 0.4487 0.0372 1.0000 Uani . . . . . .
C15 C 0.4082 0.6878 0.4150 0.0289 1.0000 Uani . . . . . .
O16 O 0.3180 0.5689 0.4031 0.0311 1.0000 Uani . . . . . .
C17 C 0.4085 0.4512 0.3913 0.0279 1.0000 Uani . . . . . .
C18 C 0.4306 0.3502 0.4392 0.0357 1.0000 Uani . . . . . .
C19 C 0.4877 0.4231 0.4899 0.0432 1.0000 Uani . . . . . .
C20 C 0.5379 0.2366 0.4208 0.0456 1.0000 Uani . . . . . .
C21 C 0.2805 0.2842 0.4510 0.0587 1.0000 Uani . . . . . .
C22 C 0.3199 0.8204 0.4062 0.0363 1.0000 Uani . . . . . .
C23 C 0.9090 0.8838 0.2722 0.0317 1.0000 Uani . . . . . .
C24 C 0.8588 0.9543 0.2264 0.0334 1.0000 Uani . . . . . .
C25 C 0.9305 0.9365 0.1773 0.0369 1.0000 Uani . . . . . .
C26 C 1.0517 0.8497 0.1733 0.0410 1.0000 Uani . . . . . .
C27 C 1.1021 0.7802 0.2188 0.0427 1.0000 Uani . . . . . .
C28 C 1.0315 0.7970 0.2682 0.0372 1.0000 Uani . . . . . .
H21 H 0.5780 0.9341 0.3483 0.0362 1.0000 Uiso R . . . . .
H22 H 0.6117 0.9133 0.2871 0.0343 1.0000 Uiso R . . . . .
H51 H 0.7646 0.6154 0.3106 0.0305 1.0000 Uiso R . . . . .
H61 H 0.7179 0.5294 0.2216 0.0470 1.0000 Uiso R . . . . .
H63 H 0.7266 0.6970 0.2213 0.0460 1.0000 Uiso R . . . . .
H62 H 0.5709 0.6193 0.2181 0.0438 1.0000 Uiso R . . . . .
H131 H 1.0026 0.5812 0.4321 0.0659 1.0000 Uiso R . . . . .
H132 H 0.9049 0.6289 0.4830 0.0651 1.0000 Uiso R . . . . .
H133 H 0.9551 0.7377 0.4392 0.0663 1.0000 Uiso R . . . . .
H151 H 0.4379 0.6842 0.4538 0.0313 1.0000 Uiso R . . . . .
H171 H 0.3642 0.3969 0.3628 0.0325 1.0000 Uiso R . . . . .
H192 H 0.5007 0.3532 0.5192 0.0632 1.0000 Uiso R . . . . .
H191 H 0.4149 0.4920 0.5020 0.0635 1.0000 Uiso R . . . . .
H193 H 0.5831 0.4686 0.4839 0.0617 1.0000 Uiso R . . . . .
H201 H 0.5427 0.1615 0.4493 0.0679 1.0000 Uiso R . . . . .
H203 H 0.6368 0.2764 0.4167 0.0660 1.0000 Uiso R . . . . .
H202 H 0.5112 0.1943 0.3862 0.0672 1.0000 Uiso R . . . . .
H211 H 0.2868 0.2166 0.4798 0.0850 1.0000 Uiso R . . . . .
H213 H 0.2111 0.3560 0.4612 0.0864 1.0000 Uiso R . . . . .
H212 H 0.2373 0.2354 0.4199 0.0883 1.0000 Uiso R . . . . .
H221 H 0.2352 0.8217 0.4315 0.0513 1.0000 Uiso R . . . . .
H222 H 0.3840 0.9002 0.4150 0.0513 1.0000 Uiso R . . . . .
H223 H 0.2824 0.8268 0.3690 0.0510 1.0000 Uiso R . . . . .
H241 H 0.7713 1.0135 0.2290 0.0391 1.0000 Uiso R . . . . .
H251 H 0.8940 0.9855 0.1459 0.0433 1.0000 Uiso R . . . . .
H261 H 1.0971 0.8380 0.1390 0.0480 1.0000 Uiso R . . . . .
H271 H 1.1882 0.7197 0.2157 0.0516 1.0000 Uiso R . . . . .
H281 H 1.0688 0.7486 0.2997 0.0457 1.0000 Uiso R . . . . .
H41 H 0.4296 0.7732 0.2727 0.0443 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.441
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.818 yes
S1 . C23 . 1.778 yes
C2 . C3 . 1.535 yes
C2 . H21 . 0.973 no
C2 . H22 . 0.952 no
C3 . O4 . 1.422 yes
C3 . C5 . 1.549 yes
C3 . C10 . 1.576 yes
O4 . H41 . 0.826 no
C5 . C6 . 1.525 yes
C5 . C7 . 1.518 yes
C5 . H51 . 0.971 no
C6 . H61 . 0.974 no
C6 . H63 . 0.989 no
C6 . H62 . 0.988 no
C7 . O8 . 1.224 yes
C7 . N9 . 1.365 yes
N9 . C10 . 1.466 yes
N9 . C17 . 1.463 yes
C10 . C11 . 1.532 yes
C10 . C15 . 1.567 yes
C11 . O12 . 1.331 yes
C11 . O14 . 1.209 yes
O12 . C13 . 1.448 yes
C13 . H131 . 0.961 no
C13 . H132 . 0.963 no
C13 . H133 . 0.973 no
C15 . O16 . 1.433 yes
C15 . C22 . 1.516 yes
C15 . H151 . 0.997 no
O16 . C17 . 1.425 yes
C17 . C18 . 1.540 yes
C17 . H171 . 0.963 no
C18 . C19 . 1.525 yes
C18 . C20 . 1.529 yes
C18 . C21 . 1.532 yes
C19 . H192 . 0.992 no
C19 . H191 . 0.981 no
C19 . H193 . 0.982 no
C20 . H201 . 1.006 no
C20 . H203 . 0.981 no
C20 . H202 . 0.976 no
C21 . H211 . 0.964 no
C21 . H213 . 0.966 no
C21 . H212 . 0.980 no
C22 . H221 . 0.992 no
C22 . H222 . 0.984 no
C22 . H223 . 0.983 no
C23 . C24 . 1.394 yes
C23 . C28 . 1.393 yes
C24 . C25 . 1.388 yes
C24 . H241 . 0.978 no
C25 . C26 . 1.383 yes
C25 . H251 . 0.965 no
C26 . C27 . 1.384 yes
C26 . H261 . 0.950 no
C27 . C28 . 1.387 yes
C27 . H271 . 0.976 no
C28 . H281 . 0.968 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C23 . 102.233 yes
S1 . C2 . C3 . 118.312 yes
S1 . C2 . H21 . 106.4 no
C3 . C2 . H21 . 108.4 no
S1 . C2 . H22 . 109.0 no
C3 . C2 . H22 . 106.5 no
H21 . C2 . H22 . 107.9 no
C2 . C3 . O4 . 108.492 yes
C2 . C3 . C5 . 117.211 yes
O4 . C3 . C5 . 108.629 yes
C2 . C3 . C10 . 115.846 yes
O4 . C3 . C10 . 104.844 yes
C5 . C3 . C10 . 100.916 yes
C3 . O4 . H41 . 109.5 no
C3 . C5 . C6 . 117.352 yes
C3 . C5 . C7 . 99.247 yes
C6 . C5 . C7 . 112.557 yes
C3 . C5 . H51 . 108.8 no
C6 . C5 . H51 . 110.3 no
C7 . C5 . H51 . 107.7 no
C5 . C6 . H61 . 108.8 no
C5 . C6 . H63 . 110.0 no
H61 . C6 . H63 . 109.8 no
C5 . C6 . H62 . 111.8 no
H61 . C6 . H62 . 108.4 no
H63 . C6 . H62 . 108.1 no
C5 . C7 . O8 . 128.205 yes
C5 . C7 . N9 . 108.509 yes
O8 . C7 . N9 . 123.220 yes
C7 . N9 . C10 . 111.738 yes
C7 . N9 . C17 . 120.947 yes
C10 . N9 . C17 . 111.772 yes
C3 . C10 . N9 . 101.753 yes
C3 . C10 . C11 . 111.161 yes
N9 . C10 . C11 . 113.011 yes
C3 . C10 . C15 . 120.421 yes
N9 . C10 . C15 . 101.907 yes
C11 . C10 . C15 . 108.145 yes
C10 . C11 . O12 . 112.886 yes
C10 . C11 . O14 . 122.380 yes
O12 . C11 . O14 . 124.731 yes
C11 . O12 . C13 . 115.846 yes
O12 . C13 . H131 . 107.3 no
O12 . C13 . H132 . 109.2 no
H131 . C13 . H132 . 113.1 no
O12 . C13 . H133 . 110.7 no
H131 . C13 . H133 . 108.3 no
H132 . C13 . H133 . 108.3 no
C10 . C15 . O16 . 104.719 yes
C10 . C15 . C22 . 119.959 yes
O16 . C15 . C22 . 109.447 yes
C10 . C15 . H151 . 105.4 no
O16 . C15 . H151 . 108.9 no
C22 . C15 . H151 . 108.0 no
C15 . O16 . C17 . 109.837 yes
N9 . C17 . O16 . 103.737 yes
N9 . C17 . C18 . 115.221 yes
O16 . C17 . C18 . 114.474 yes
N9 . C17 . H171 . 107.6 no
O16 . C17 . H171 . 109.5 no
C18 . C17 . H171 . 106.1 no
C17 . C18 . C19 . 112.843 yes
C17 . C18 . C20 . 107.528 yes
C19 . C18 . C20 . 110.595 yes
C17 . C18 . C21 . 106.716 yes
C19 . C18 . C21 . 109.634 yes
C20 . C18 . C21 . 109.398 yes
C18 . C19 . H192 . 109.4 no
C18 . C19 . H191 . 109.1 no
H192 . C19 . H191 . 108.2 no
C18 . C19 . H193 . 112.3 no
H192 . C19 . H193 . 107.7 no
H191 . C19 . H193 . 110.1 no
C18 . C20 . H201 . 109.1 no
C18 . C20 . H203 . 109.8 no
H201 . C20 . H203 . 108.0 no
C18 . C20 . H202 . 113.3 no
H201 . C20 . H202 . 109.0 no
H203 . C20 . H202 . 107.4 no
C18 . C21 . H211 . 111.3 no
C18 . C21 . H213 . 109.8 no
H211 . C21 . H213 . 108.8 no
C18 . C21 . H212 . 113.9 no
H211 . C21 . H212 . 106.4 no
H213 . C21 . H212 . 106.5 no
C15 . C22 . H221 . 109.3 no
C15 . C22 . H222 . 107.8 no
H221 . C22 . H222 . 108.2 no
C15 . C22 . H223 . 111.6 no
H221 . C22 . H223 . 108.6 no
H222 . C22 . H223 . 111.2 no
S1 . C23 . C24 . 122.315 yes
S1 . C23 . C28 . 118.206 yes
C24 . C23 . C28 . 119.429 yes
C23 . C24 . C25 . 119.740 yes
C23 . C24 . H241 . 119.6 no
C25 . C24 . H241 . 120.7 no
C24 . C25 . C26 . 120.702 yes
C24 . C25 . H251 . 118.7 no
C26 . C25 . H251 . 120.6 no
C25 . C26 . C27 . 119.650 yes
C25 . C26 . H261 . 118.7 no
C27 . C26 . H261 . 121.6 no
C26 . C27 . C28 . 120.305 yes
C26 . C27 . H271 . 119.1 no
C28 . C27 . H271 . 120.6 no
C23 . C28 . C27 . 120.173 yes
C23 . C28 . H281 . 120.5 no
C27 . C28 . H281 . 119.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C25 0_555 H251 . O16 3_655 147 0.97 2.41 3.2639(16) yes
O4 0_555 H41 . O8 . 178 0.83 1.93 2.7595(16) yes
_database_code_depnum_ccdc_archive 'CCDC 952083'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6326
_audit_creation_date             12-04-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6326
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   9.1567(1)
_cell_length_b                   13.7873(1)
_cell_length_c                   17.7687(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2243.23(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C23 H33 N1 O6 
# Dc =      1.24 Fooo =    904.00 Mu =      7.29 M =    419.52
# Found Formula = C23 H33 N1 O6 
# Dc =      1.24 FOOO =    904.00 Mu =      7.29 M =    419.52

_chemical_formula_sum            'C23 H33 N1 O6'
_chemical_formula_moiety         'C23 H33 N1 O6'
_chemical_compound_source        .
_chemical_formula_weight         419.52


_cell_measurement_reflns_used    32754
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          1.00

_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.729

# Sheldrick geometric approximatio 0.93 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            55832
_reflns_number_total             4712
_diffrn_reflns_av_R_equivalents  0.035
# Number of reflections without Friedels Law is 4712 
# Number of reflections with Friedels Law is 2682 
# Theoretical number of reflections is about 2360 


_diffrn_reflns_theta_min         4.058
_diffrn_reflns_theta_max         76.585
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        76.585
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   2.26
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.19
_refine_diff_density_max         0.17


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     0
_refine_ls_number_parameters     272
_oxford_refine_ls_R_factor_ref   0.0286
_refine_ls_wR_factor_ref         0.0744
_refine_ls_goodness_of_fit_ref   0.9939
_refine_ls_shift/su_max          0.0003526
_refine_ls_shift/su_mean         0.0000482


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4710
_refine_ls_R_factor_all          0.0286
_refine_ls_wR_factor_all         0.0745

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4604
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_gt          0.0735

_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_abs_structure_details 'Flack (1983), 2030 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.46P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.4097 0.3411 0.4851 0.0218 1.0000 Uani . . . . . .
C2 C 0.4641 0.3670 0.4133 0.0188 1.0000 Uani . . . . . .
C3 C 0.3493 0.3419 0.3532 0.0215 1.0000 Uani . . . . . .
O4 O 0.3988 0.3698 0.2807 0.0269 1.0000 Uani . . . . . .
C5 C 0.4180 0.2936 0.2286 0.0481 1.0000 Uani . . . . . .
C6 C 0.1992 0.3884 0.3673 0.0270 1.0000 Uani . . . . . .
C7 C 0.0846 0.3416 0.3184 0.0251 1.0000 Uani . . . . . .
C8 C 0.0419 0.3828 0.2505 0.0331 1.0000 Uani . . . . . .
C9 C -0.0568 0.3360 0.2038 0.0376 1.0000 Uani . . . . . .
C10 C -0.1167 0.2477 0.2244 0.0347 1.0000 Uani . . . . . .
C11 C -0.0746 0.2058 0.2917 0.0363 1.0000 Uani . . . . . .
C12 C 0.0250 0.2524 0.3384 0.0325 1.0000 Uani . . . . . .
C13 C 0.6133 0.3160 0.4021 0.0210 1.0000 Uani . . . . . .
C14 C 0.7064 0.3742 0.4566 0.0209 1.0000 Uani . . . . . .
O15 O 0.8044 0.3451 0.4980 0.0280 1.0000 Uani . . . . . .
N16 N 0.6603 0.4676 0.4521 0.0190 1.0000 Uani . . . . . .
C17 C 0.5135 0.4766 0.4194 0.0186 1.0000 Uani . . . . . .
C18 C 0.5202 0.5247 0.3409 0.0228 1.0000 Uani . . . . . .
O19 O 0.4282 0.5797 0.3175 0.0309 1.0000 Uani . . . . . .
O20 O 0.6388 0.4979 0.3031 0.0278 1.0000 Uani . . . . . .
C21 C 0.6457 0.5273 0.2254 0.0427 1.0000 Uani . . . . . .
C22 C 0.4417 0.5499 0.4746 0.0208 1.0000 Uani . . . . . .
O23 O 0.5668 0.6085 0.4949 0.0231 1.0000 Uani . . . . . .
C24 C 0.6914 0.5483 0.5036 0.0197 1.0000 Uani . . . . . .
C25 C 0.8287 0.6087 0.4874 0.0238 1.0000 Uani . . . . . .
C26 C 0.9645 0.5460 0.4966 0.0395 1.0000 Uani . . . . . .
C27 C 0.8339 0.6903 0.5461 0.0329 1.0000 Uani . . . . . .
C28 C 0.8240 0.6528 0.4090 0.0427 1.0000 Uani . . . . . .
C29 C 0.3661 0.5169 0.5461 0.0274 1.0000 Uani . . . . . .
C30 C 0.6148 0.2070 0.4153 0.0275 1.0000 Uani . . . . . .
H11 H 0.3793 0.2849 0.4850 0.0346 1.0000 Uiso R . . . . .
H31 H 0.3379 0.2707 0.3546 0.0234 1.0000 Uiso R . . . . .
H51 H 0.5021 0.2518 0.2433 0.0720 1.0000 Uiso R . . . . .
H52 H 0.4371 0.3238 0.1808 0.0706 1.0000 Uiso R . . . . .
H53 H 0.3273 0.2540 0.2247 0.0714 1.0000 Uiso R . . . . .
H61 H 0.2052 0.4588 0.3576 0.0304 1.0000 Uiso R . . . . .
H62 H 0.1763 0.3784 0.4207 0.0316 1.0000 Uiso R . . . . .
H81 H 0.0837 0.4430 0.2358 0.0411 1.0000 Uiso R . . . . .
H91 H -0.0844 0.3660 0.1573 0.0461 1.0000 Uiso R . . . . .
H101 H -0.1860 0.2165 0.1916 0.0406 1.0000 Uiso R . . . . .
H111 H -0.1132 0.1430 0.3063 0.0445 1.0000 Uiso R . . . . .
H121 H 0.0538 0.2221 0.3863 0.0392 1.0000 Uiso R . . . . .
H131 H 0.6486 0.3310 0.3509 0.0234 1.0000 Uiso R . . . . .
H211 H 0.7244 0.4902 0.2016 0.0651 1.0000 Uiso R . . . . .
H212 H 0.6568 0.5950 0.2214 0.0657 1.0000 Uiso R . . . . .
H213 H 0.5537 0.5100 0.2012 0.0655 1.0000 Uiso R . . . . .
H221 H 0.3743 0.5920 0.4462 0.0236 1.0000 Uiso R . . . . .
H241 H 0.6976 0.5233 0.5559 0.0230 1.0000 Uiso R . . . . .
H261 H 1.0535 0.5856 0.4900 0.0576 1.0000 Uiso R . . . . .
H262 H 0.9644 0.4954 0.4571 0.0574 1.0000 Uiso R . . . . .
H263 H 0.9648 0.5143 0.5491 0.0592 1.0000 Uiso R . . . . .
H271 H 0.8346 0.6647 0.5999 0.0504 1.0000 Uiso R . . . . .
H272 H 0.9230 0.7270 0.5387 0.0489 1.0000 Uiso R . . . . .
H273 H 0.7491 0.7334 0.5380 0.0502 1.0000 Uiso R . . . . .
H281 H 0.8292 0.6024 0.3716 0.0637 1.0000 Uiso R . . . . .
H282 H 0.9087 0.6953 0.4020 0.0612 1.0000 Uiso R . . . . .
H283 H 0.7333 0.6909 0.4020 0.0636 1.0000 Uiso R . . . . .
H291 H 0.4294 0.4756 0.5763 0.0405 1.0000 Uiso R . . . . .
H292 H 0.2758 0.4830 0.5343 0.0380 1.0000 Uiso R . . . . .
H293 H 0.3443 0.5760 0.5747 0.0394 1.0000 Uiso R . . . . .
H301 H 0.7122 0.1830 0.4130 0.0396 1.0000 Uiso R . . . . .
H302 H 0.5744 0.1891 0.4644 0.0415 1.0000 Uiso R . . . . .
H303 H 0.5569 0.1723 0.3785 0.0419 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.003
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.415 yes
O1 . H11 . 0.823 no
C2 . C3 . 1.539 yes
C2 . C13 . 1.549 yes
C2 . C17 . 1.580 yes
C3 . O4 . 1.419 yes
C3 . C6 . 1.537 yes
C3 . H31 . 0.987 no
O4 . C5 . 1.410 yes
C5 . H51 . 0.997 no
C5 . H52 . 0.962 no
C5 . H53 . 0.996 no
C6 . C7 . 1.507 yes
C6 . H61 . 0.987 no
C6 . H62 . 0.981 no
C7 . C8 . 1.390 yes
C7 . C12 . 1.393 yes
C8 . C9 . 1.386 yes
C8 . H81 . 0.951 no
C9 . C10 . 1.384 yes
C9 . H91 . 0.958 no
C10 . C11 . 1.384 yes
C10 . H101 . 0.964 no
C11 . C12 . 1.390 yes
C11 . H111 . 0.971 no
C12 . H121 . 0.983 no
C13 . C14 . 1.519 yes
C13 . C30 . 1.521 yes
C13 . H131 . 0.987 no
C14 . O15 . 1.228 yes
C14 . N16 . 1.357 yes
N16 . C17 . 1.469 yes
N16 . C24 . 1.469 yes
C17 . C18 . 1.547 yes
C17 . C22 . 1.554 yes
C18 . O19 . 1.207 yes
C18 . O20 . 1.329 yes
O20 . C21 . 1.441 yes
C21 . H211 . 0.980 no
C21 . H212 . 0.941 no
C21 . H213 . 0.976 no
C22 . O23 . 1.447 yes
C22 . C29 . 1.516 yes
C22 . H221 . 0.986 no
O23 . C24 . 1.420 yes
C24 . C25 . 1.536 yes
C24 . H241 . 0.992 no
C25 . C26 . 1.523 yes
C25 . C27 . 1.534 yes
C25 . C28 . 1.520 yes
C26 . H261 . 0.988 no
C26 . H262 . 0.989 no
C26 . H263 . 1.031 no
C27 . H271 . 1.019 no
C27 . H272 . 0.969 no
C27 . H273 . 0.989 no
C28 . H281 . 0.963 no
C28 . H282 . 0.980 no
C28 . H283 . 0.991 no
C29 . H291 . 0.974 no
C29 . H292 . 0.972 no
C29 . H293 . 0.981 no
C30 . H301 . 0.952 no
C30 . H302 . 0.979 no
C30 . H303 . 0.969 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 110.8 no
O1 . C2 . C3 . 109.162 yes
O1 . C2 . C13 . 108.163 yes
C3 . C2 . C13 . 114.265 yes
O1 . C2 . C17 . 106.274 yes
C3 . C2 . C17 . 117.295 yes
C13 . C2 . C17 . 100.980 yes
C2 . C3 . O4 . 110.543 yes
C2 . C3 . C6 . 113.803 yes
O4 . C3 . C6 . 108.738 yes
C2 . C3 . H31 . 106.1 no
O4 . C3 . H31 . 109.0 no
C6 . C3 . H31 . 108.5 no
C3 . O4 . C5 . 115.720 yes
O4 . C5 . H51 . 110.8 no
O4 . C5 . H52 . 106.3 no
H51 . C5 . H52 . 109.9 no
O4 . C5 . H53 . 110.5 no
H51 . C5 . H53 . 110.2 no
H52 . C5 . H53 . 109.1 no
C3 . C6 . C7 . 110.478 yes
C3 . C6 . H61 . 109.4 no
C7 . C6 . H61 . 111.0 no
C3 . C6 . H62 . 106.9 no
C7 . C6 . H62 . 110.4 no
H61 . C6 . H62 . 108.6 no
C6 . C7 . C8 . 121.445 yes
C6 . C7 . C12 . 120.236 yes
C8 . C7 . C12 . 118.208 yes
C7 . C8 . C9 . 120.894 yes
C7 . C8 . H81 . 118.8 no
C9 . C8 . H81 . 120.3 no
C8 . C9 . C10 . 120.598 yes
C8 . C9 . H91 . 119.2 no
C10 . C9 . H91 . 120.2 no
C9 . C10 . C11 . 119.044 yes
C9 . C10 . H101 . 119.6 no
C11 . C10 . H101 . 121.3 no
C10 . C11 . C12 . 120.406 yes
C10 . C11 . H111 . 120.1 no
C12 . C11 . H111 . 119.5 no
C7 . C12 . C11 . 120.840 yes
C7 . C12 . H121 . 119.4 no
C11 . C12 . H121 . 119.7 no
C2 . C13 . C14 . 99.988 yes
C2 . C13 . C30 . 115.873 yes
C14 . C13 . C30 . 114.737 yes
C2 . C13 . H131 . 108.2 no
C14 . C13 . H131 . 107.1 no
C30 . C13 . H131 . 110.2 no
C13 . C14 . O15 . 128.287 yes
C13 . C14 . N16 . 106.777 yes
O15 . C14 . N16 . 124.933 yes
C14 . N16 . C17 . 112.849 yes
C14 . N16 . C24 . 128.465 yes
C17 . N16 . C24 . 111.059 yes
C2 . C17 . N16 . 101.993 yes
C2 . C17 . C18 . 111.027 yes
N16 . C17 . C18 . 110.914 yes
C2 . C17 . C22 . 122.958 yes
N16 . C17 . C22 . 101.111 yes
C18 . C17 . C22 . 107.904 yes
C17 . C18 . O19 . 123.544 yes
C17 . C18 . O20 . 111.631 yes
O19 . C18 . O20 . 124.825 yes
C18 . O20 . C21 . 116.184 yes
O20 . C21 . H211 . 107.4 no
O20 . C21 . H212 . 110.9 no
H211 . C21 . H212 . 113.9 no
O20 . C21 . H213 . 108.4 no
H211 . C21 . H213 . 108.5 no
H212 . C21 . H213 . 107.6 no
C17 . C22 . O23 . 100.707 yes
C17 . C22 . C29 . 121.762 yes
O23 . C22 . C29 . 108.711 yes
C17 . C22 . H221 . 108.9 no
O23 . C22 . H221 . 107.1 no
C29 . C22 . H221 . 108.6 no
C22 . O23 . C24 . 109.629 yes
N16 . C24 . O23 . 102.671 yes
N16 . C24 . C25 . 116.931 yes
O23 . C24 . C25 . 108.647 yes
N16 . C24 . H241 . 109.3 no
O23 . C24 . H241 . 110.6 no
C25 . C24 . H241 . 108.5 no
C24 . C25 . C26 . 109.882 yes
C24 . C25 . C27 . 107.185 yes
C26 . C25 . C27 . 108.549 yes
C24 . C25 . C28 . 111.455 yes
C26 . C25 . C28 . 110.355 yes
C27 . C25 . C28 . 109.317 yes
C25 . C26 . H261 . 110.3 no
C25 . C26 . H262 . 108.9 no
H261 . C26 . H262 . 107.8 no
C25 . C26 . H263 . 109.9 no
H261 . C26 . H263 . 109.8 no
H262 . C26 . H263 . 110.1 no
C25 . C27 . H271 . 112.6 no
C25 . C27 . H272 . 108.5 no
H271 . C27 . H272 . 107.7 no
C25 . C27 . H273 . 108.5 no
H271 . C27 . H273 . 110.5 no
H272 . C27 . H273 . 109.0 no
C25 . C28 . H281 . 110.0 no
C25 . C28 . H282 . 109.5 no
H281 . C28 . H282 . 107.8 no
C25 . C28 . H283 . 110.5 no
H281 . C28 . H283 . 109.7 no
H282 . C28 . H283 . 109.3 no
C22 . C29 . H291 . 111.4 no
C22 . C29 . H292 . 110.6 no
H291 . C29 . H292 . 110.1 no
C22 . C29 . H293 . 106.1 no
H291 . C29 . H293 . 108.7 no
H292 . C29 . H293 . 109.8 no
C13 . C30 . H301 . 110.2 no
C13 . C30 . H302 . 112.5 no
H301 . C30 . H302 . 107.7 no
C13 . C30 . H303 . 112.3 no
H301 . C30 . H303 . 108.2 no
H302 . C30 . H303 . 105.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O1 . H11 . O15 0_456 171 0.82 1.94 2.7580(19) yes
C13 0_555 H131 . O20 0_555 120 0.99 2.45 3.0713(19) yes
C28 0_555 H281 . O20 . 134 0.96 2.57 3.3138(19) yes
C30 0_555 H301 . O1 2_556 132 0.95 2.58 3.2964(19) yes
_database_code_depnum_ccdc_archive 'CCDC 980818'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6325
_audit_creation_date             11-10-29
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 6325
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.92170(10)
_cell_length_b                   13.25210(10)
_cell_length_c                   15.20210(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2200.28(3)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C23 H33 N1 O6 
# Dc =      1.27 Fooo =    904.00 Mu =      7.43 M =    419.52
# Found Formula = C23 H33 N1 O6 
# Dc =      1.27 FOOO =    904.00 Mu =      7.43 M =    419.52

_chemical_formula_sum            'C23 H33 N1 O6'
_chemical_formula_moiety         'C23 H33 N1 O6'
_chemical_compound_source        .
_chemical_formula_weight         419.52


_cell_measurement_reflns_used    11933
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_max          0.050

_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.743

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            20572
_reflns_number_total             4586
_diffrn_reflns_av_R_equivalents  0.026
# Number of reflections without Friedels Law is 4586 
# Number of reflections with Friedels Law is 2610 
# Theoretical number of reflections is about 2312 


_diffrn_reflns_theta_min         4.426
_diffrn_reflns_theta_max         76.489
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        76.489
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.17


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_number_parameters     272
_oxford_refine_ls_R_factor_ref   0.0276
_refine_ls_wR_factor_ref         0.0678
_refine_ls_goodness_of_fit_ref   1.0118
_refine_ls_shift/su_max          0.0005621
_refine_ls_shift/su_mean         0.0000603


# The values computed from all data 
_oxford_reflns_number_all        4586
_refine_ls_R_factor_all          0.0276
_refine_ls_wR_factor_all         0.0678

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4440
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_gt          0.0670

_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_abs_structure_details 'Flack (1983), 1976 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.28P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.5009 0.7126 0.4554 0.0198 1.0000 Uani . . . . . .
C2 C 0.4119 0.6663 0.3959 0.0222 1.0000 Uani . . . . . .
O3 O 0.3380 0.6063 0.4529 0.0229 1.0000 Uani . . . . . .
C4 C 0.4093 0.5746 0.5273 0.0202 1.0000 Uani . . . . . .
C5 C 0.5052 0.6608 0.5405 0.0178 1.0000 Uani . . . . . .
C6 C 0.4788 0.7497 0.6075 0.0185 1.0000 Uani . . . . . .
C7 C 0.5424 0.8387 0.5599 0.0222 1.0000 Uani . . . . . .
C8 C 0.5136 0.8157 0.4636 0.0213 1.0000 Uani . . . . . .
C9 C 0.4668 0.6080 0.3176 0.0273 1.0000 Uani . . . . . .
C10 C 0.5400 0.6836 0.2622 0.0372 1.0000 Uani . . . . . .
C11 C 0.3600 0.5658 0.2636 0.0384 1.0000 Uani . . . . . .
C12 C 0.5509 0.5210 0.3448 0.0391 1.0000 Uani . . . . . .
C13 C 0.3239 0.5466 0.6017 0.0246 1.0000 Uani . . . . . .
C14 C 0.6334 0.6151 0.5534 0.0199 1.0000 Uani . . . . . .
O15 O 0.7251 0.6460 0.5187 0.0274 1.0000 Uani . . . . . .
O16 O 0.6299 0.5332 0.6042 0.0243 1.0000 Uani . . . . . .
C17 C 0.7463 0.4812 0.6142 0.0339 1.0000 Uani . . . . . .
C18 C 0.5216 0.7280 0.7019 0.0206 1.0000 Uani . . . . . .
O19 O 0.6515 0.7188 0.6991 0.0251 1.0000 Uani . . . . . .
C20 C 0.7004 0.6658 0.7726 0.0357 1.0000 Uani . . . . . .
C21 C 0.4806 0.8088 0.7687 0.0251 1.0000 Uani . . . . . .
C22 C 0.4379 0.7672 0.8560 0.0229 1.0000 Uani . . . . . .
C23 C 0.3351 0.7046 0.8600 0.0281 1.0000 Uani . . . . . .
C24 C 0.2942 0.6676 0.9403 0.0353 1.0000 Uani . . . . . .
C25 C 0.3547 0.6926 1.0172 0.0395 1.0000 Uani . . . . . .
C26 C 0.4565 0.7542 1.0140 0.0381 1.0000 Uani . . . . . .
C27 C 0.4977 0.7911 0.9337 0.0307 1.0000 Uani . . . . . .
O28 O 0.3513 0.7652 0.6158 0.0210 1.0000 Uani . . . . . .
C29 C 0.5045 0.9456 0.5853 0.0310 1.0000 Uani . . . . . .
O30 O 0.5012 0.8754 0.4038 0.0274 1.0000 Uani . . . . . .
H172 H 0.7391 0.4366 0.6648 0.0546 1.0000 Uiso R . . . . .
H173 H 0.8088 0.5294 0.6247 0.0530 1.0000 Uiso R . . . . .
H171 H 0.7640 0.4447 0.5609 0.0543 1.0000 Uiso R . . . . .
H21 H 0.3583 0.7215 0.3709 0.0266 1.0000 Uiso R . . . . .
H41 H 0.4600 0.5133 0.5106 0.0227 1.0000 Uiso R . . . . .
H133 H 0.3723 0.5221 0.6521 0.0352 1.0000 Uiso R . . . . .
H131 H 0.2708 0.4927 0.5822 0.0355 1.0000 Uiso R . . . . .
H132 H 0.2734 0.6018 0.6219 0.0362 1.0000 Uiso R . . . . .
H113 H 0.3866 0.5307 0.2106 0.0597 1.0000 Uiso R . . . . .
H112 H 0.3121 0.5189 0.2993 0.0586 1.0000 Uiso R . . . . .
H111 H 0.3045 0.6211 0.2472 0.0595 1.0000 Uiso R . . . . .
H121 H 0.6187 0.5443 0.3810 0.0591 1.0000 Uiso R . . . . .
H122 H 0.5847 0.4892 0.2922 0.0582 1.0000 Uiso R . . . . .
H123 H 0.5048 0.4703 0.3770 0.0580 1.0000 Uiso R . . . . .
H101 H 0.4889 0.7419 0.2459 0.0574 1.0000 Uiso R . . . . .
H103 H 0.5694 0.6512 0.2094 0.0566 1.0000 Uiso R . . . . .
H102 H 0.6101 0.7057 0.2937 0.0570 1.0000 Uiso R . . . . .
H71 H 0.6321 0.8320 0.5664 0.0259 1.0000 Uiso R . . . . .
H281 H 0.3206 0.7869 0.5708 0.0326 1.0000 Uiso R . . . . .
H181 H 0.4857 0.6621 0.7191 0.0233 1.0000 Uiso R . . . . .
H202 H 0.6887 0.7025 0.8287 0.0539 1.0000 Uiso R . . . . .
H203 H 0.7869 0.6560 0.7636 0.0531 1.0000 Uiso R . . . . .
H201 H 0.6638 0.5980 0.7789 0.0530 1.0000 Uiso R . . . . .
H212 H 0.4101 0.8461 0.7424 0.0290 1.0000 Uiso R . . . . .
H211 H 0.5503 0.8575 0.7779 0.0294 1.0000 Uiso R . . . . .
H231 H 0.2927 0.6879 0.8066 0.0347 1.0000 Uiso R . . . . .
H241 H 0.2232 0.6241 0.9416 0.0434 1.0000 Uiso R . . . . .
H251 H 0.3255 0.6653 1.0729 0.0466 1.0000 Uiso R . . . . .
H261 H 0.5022 0.7729 1.0665 0.0437 1.0000 Uiso R . . . . .
H271 H 0.5720 0.8340 0.9308 0.0379 1.0000 Uiso R . . . . .
H291 H 0.4146 0.9491 0.5857 0.0487 1.0000 Uiso R . . . . .
H292 H 0.5376 0.9914 0.5421 0.0472 1.0000 Uiso R . . . . .
H293 H 0.5382 0.9615 0.6424 0.0479 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.361
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.463 yes
N1 . C5 . 1.465 yes
N1 . C8 . 1.379 yes
C2 . O3 . 1.427 yes
C2 . C9 . 1.541 yes
C2 . H21 . 1.011 no
O3 . C4 . 1.436 yes
C4 . C5 . 1.562 yes
C4 . C13 . 1.512 yes
C4 . H41 . 1.017 no
C5 . C6 . 1.584 yes
C5 . C14 . 1.538 yes
C6 . C7 . 1.549 yes
C6 . C18 . 1.537 yes
C6 . O28 . 1.413 yes
C7 . C8 . 1.527 yes
C7 . C29 . 1.525 yes
C7 . H71 . 0.988 no
C8 . O30 . 1.214 yes
C9 . C10 . 1.534 yes
C9 . C11 . 1.533 yes
C9 . C12 . 1.531 yes
C10 . H101 . 0.984 no
C10 . H103 . 0.965 no
C10 . H102 . 0.949 no
C11 . H113 . 0.975 no
C11 . H112 . 0.978 no
C11 . H111 . 0.984 no
C12 . H121 . 0.972 no
C12 . H122 . 0.976 no
C12 . H123 . 0.973 no
C13 . H133 . 0.985 no
C13 . H131 . 0.967 no
C13 . H132 . 0.966 no
C14 . O15 . 1.204 yes
C14 . O16 . 1.332 yes
O16 . C17 . 1.453 yes
C17 . H172 . 0.973 no
C17 . H173 . 0.949 no
C17 . H171 . 0.965 no
C18 . O19 . 1.425 yes
C18 . C21 . 1.541 yes
C18 . H181 . 0.992 no
O19 . C20 . 1.423 yes
C20 . H202 . 0.990 no
C20 . H203 . 0.964 no
C20 . H201 . 0.987 no
C21 . C22 . 1.511 yes
C21 . H212 . 0.998 no
C21 . H211 . 1.009 no
C22 . C23 . 1.397 yes
C22 . C27 . 1.386 yes
C23 . C24 . 1.388 yes
C23 . H231 . 0.961 no
C24 . C25 . 1.383 yes
C24 . H241 . 0.966 no
C25 . C26 . 1.381 yes
C25 . H251 . 0.974 no
C26 . C27 . 1.391 yes
C26 . H261 . 0.973 no
C27 . H271 . 0.992 no
O28 . H281 . 0.814 no
C29 . H291 . 0.983 no
C29 . H292 . 0.964 no
C29 . H293 . 0.966 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 111.781 yes
C2 . N1 . C8 . 122.511 yes
C5 . N1 . C8 . 112.436 yes
N1 . C2 . O3 . 103.495 yes
N1 . C2 . C9 . 115.437 yes
O3 . C2 . C9 . 114.205 yes
N1 . C2 . H21 . 108.3 no
O3 . C2 . H21 . 107.7 no
C9 . C2 . H21 . 107.3 no
C2 . O3 . C4 . 109.551 yes
O3 . C4 . C5 . 104.551 yes
O3 . C4 . C13 . 109.044 yes
C5 . C4 . C13 . 119.798 yes
O3 . C4 . H41 . 109.4 no
C5 . C4 . H41 . 104.5 no
C13 . C4 . H41 . 109.1 no
C4 . C5 . N1 . 102.011 yes
C4 . C5 . C6 . 120.300 yes
N1 . C5 . C6 . 102.313 yes
C4 . C5 . C14 . 109.802 yes
N1 . C5 . C14 . 109.014 yes
C6 . C5 . C14 . 112.109 yes
C5 . C6 . C7 . 100.625 yes
C5 . C6 . C18 . 113.977 yes
C7 . C6 . C18 . 116.308 yes
C5 . C6 . O28 . 110.094 yes
C7 . C6 . O28 . 111.902 yes
C18 . C6 . O28 . 104.120 yes
C6 . C7 . C8 . 101.736 yes
C6 . C7 . C29 . 117.839 yes
C8 . C7 . C29 . 111.854 yes
C6 . C7 . H71 . 109.2 no
C8 . C7 . H71 . 106.4 no
C29 . C7 . H71 . 109.1 no
C7 . C8 . N1 . 107.774 yes
C7 . C8 . O30 . 127.623 yes
N1 . C8 . O30 . 124.590 yes
C2 . C9 . C10 . 107.424 yes
C2 . C9 . C11 . 107.504 yes
C10 . C9 . C11 . 109.967 yes
C2 . C9 . C12 . 113.731 yes
C10 . C9 . C12 . 109.103 yes
C11 . C9 . C12 . 109.064 yes
C9 . C10 . H101 . 110.8 no
C9 . C10 . H103 . 109.8 no
H101 . C10 . H103 . 109.2 no
C9 . C10 . H102 . 110.2 no
H101 . C10 . H102 . 110.1 no
H103 . C10 . H102 . 106.8 no
C9 . C11 . H113 . 113.0 no
C9 . C11 . H112 . 110.0 no
H113 . C11 . H112 . 108.4 no
C9 . C11 . H111 . 109.4 no
H113 . C11 . H111 . 109.3 no
H112 . C11 . H111 . 106.6 no
C9 . C12 . H121 . 111.8 no
C9 . C12 . H122 . 109.3 no
H121 . C12 . H122 . 108.2 no
C9 . C12 . H123 . 110.2 no
H121 . C12 . H123 . 109.2 no
H122 . C12 . H123 . 108.1 no
C4 . C13 . H133 . 109.3 no
C4 . C13 . H131 . 108.8 no
H133 . C13 . H131 . 108.4 no
C4 . C13 . H132 . 113.8 no
H133 . C13 . H132 . 108.1 no
H131 . C13 . H132 . 108.3 no
C5 . C14 . O15 . 124.589 yes
C5 . C14 . O16 . 111.629 yes
O15 . C14 . O16 . 123.693 yes
C14 . O16 . C17 . 114.955 yes
O16 . C17 . H172 . 107.5 no
O16 . C17 . H173 . 109.1 no
H172 . C17 . H173 . 109.6 no
O16 . C17 . H171 . 109.0 no
H172 . C17 . H171 . 112.0 no
H173 . C17 . H171 . 109.5 no
C6 . C18 . O19 . 106.904 yes
C6 . C18 . C21 . 113.360 yes
O19 . C18 . C21 . 111.662 yes
C6 . C18 . H181 . 106.8 no
O19 . C18 . H181 . 109.0 no
C21 . C18 . H181 . 108.9 no
C18 . O19 . C20 . 113.073 yes
O19 . C20 . H202 . 112.7 no
O19 . C20 . H203 . 108.9 no
H202 . C20 . H203 . 108.3 no
O19 . C20 . H201 . 112.0 no
H202 . C20 . H201 . 108.1 no
H203 . C20 . H201 . 106.7 no
C18 . C21 . C22 . 114.511 yes
C18 . C21 . H212 . 107.8 no
C22 . C21 . H212 . 107.1 no
C18 . C21 . H211 . 108.5 no
C22 . C21 . H211 . 110.1 no
H212 . C21 . H211 . 108.7 no
C21 . C22 . C23 . 120.212 yes
C21 . C22 . C27 . 121.280 yes
C23 . C22 . C27 . 118.500 yes
C22 . C23 . C24 . 120.445 yes
C22 . C23 . H231 . 119.1 no
C24 . C23 . H231 . 120.4 no
C23 . C24 . C25 . 120.305 yes
C23 . C24 . H241 . 119.1 no
C25 . C24 . H241 . 120.6 no
C24 . C25 . C26 . 119.809 yes
C24 . C25 . H251 . 119.4 no
C26 . C25 . H251 . 120.8 no
C25 . C26 . C27 . 119.908 yes
C25 . C26 . H261 . 122.4 no
C27 . C26 . H261 . 117.7 no
C26 . C27 . C22 . 121.032 yes
C26 . C27 . H271 . 120.3 no
C22 . C27 . H271 . 118.7 no
C6 . O28 . H281 . 112.5 no
C7 . C29 . H291 . 108.4 no
C7 . C29 . H292 . 108.1 no
H291 . C29 . H292 . 110.5 no
C7 . C29 . H293 . 109.0 no
H291 . C29 . H293 . 111.4 no
H292 . C29 . H293 . 109.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C17 0_555 H173 . O30 0_566 157 0.95 2.49 3.3817(17) yes
C7 0_555 H71 . O3 2_566 152 0.99 2.41 3.3149(17) yes
O28 0_555 H281 . O15 0_466 168 0.81 1.93 2.7320(17) yes
_database_code_depnum_ccdc_archive 'CCDC 980819'
