# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16
_database_code_depnum_ccdc_archive 'CCDC 1507899'
_audit_update_record             
;
2016-10-03 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2016-10-03
_audit_creation_method           CRYSTALS_ver_14.61_build_6019

_oxford_structure_analysis_title 030djd16
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.2373(3)
_cell_length_b                   36.3214(19)
_cell_length_c                   8.6667(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.598(4)
_cell_angle_gamma                90
_cell_volume                     1957.10(16)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,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 = C22 H25 N1 O5 
# Dc =      1.30 Fooo =    816.00 Mu =      7.54 M =    383.44
# Found Formula = C22 H25 N1 O5 
# Dc =      1.30 FOOO =    816.00 Mu =      7.54 M =    383.44

_chemical_formula_sum            'C22 H25 N1 O5'
_chemical_formula_moiety         'C22 H25 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         383.44


_cell_measurement_reflns_used    6618
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_max          0.18

_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.754

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.76
_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     1.54184
_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       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            24541
_reflns_number_total             4064
_diffrn_reflns_av_R_equivalents  0.049
# Number of reflections with Friedels Law is 4064 
# Theoretical number of reflections is about 8238 


_diffrn_reflns_theta_min         4.870
_diffrn_reflns_theta_max         76.622
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        75.089
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              45
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   2.40
_oxford_diffrn_Wilson_scale      0.04

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.31


# 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         4061
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0626
_refine_ls_wR_factor_ref         0.1311
_refine_ls_goodness_of_fit_ref   0.9350
_refine_ls_shift/su_max          0.0005968
_refine_ls_shift/su_mean         0.0000558


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4061
_refine_ls_R_factor_all          0.0626
_refine_ls_wR_factor_all         0.1311

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3425
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_gt          0.1262

# 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 .


_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) + ( 0.01P)² + 4.77P] 
 ,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
C1 C 0.1187(4) 0.61213(6) 0.1241(3) 0.0239 1.0000 Uani . . . . . .
C2 C 0.1313(4) 0.58692(7) -0.0182(3) 0.0280 1.0000 Uani . . . . . .
C3 C 0.1256(4) 0.60753(7) -0.1685(3) 0.0259 1.0000 Uani . . . . . .
C4 C -0.0410(4) 0.60739(8) -0.2737(3) 0.0336 1.0000 Uani . . . . . .
C5 C 0.3289(4) 0.62647(7) -0.2006(3) 0.0269 1.0000 Uani . . . . . .
O6 O 0.4979(3) 0.62148(6) -0.1243(2) 0.0388 1.0000 Uani . . . . . .
O7 O 0.3081(3) 0.64881(5) -0.3238(2) 0.0335 1.0000 Uani . . . . . .
C8 C 0.5025(4) 0.66624(8) -0.3704(3) 0.0352 1.0000 Uani . . . . . .
C9 C 0.5541(6) 0.70029(11) -0.2808(4) 0.0617 1.0000 Uani . . . . . .
N10 N -0.0976(3) 0.62688(6) 0.1266(2) 0.0253 1.0000 Uani . . . . . .
C11 C -0.1338(4) 0.65896(6) 0.2097(3) 0.0234 1.0000 Uani . . . . . .
C12 C -0.3213(4) 0.67949(7) 0.1763(3) 0.0262 1.0000 Uani . . . . . .
C13 C -0.3621(4) 0.71151(7) 0.2561(3) 0.0287 1.0000 Uani . . . . . .
C14 C -0.2152(4) 0.72369(7) 0.3739(3) 0.0289 1.0000 Uani . . . . . .
C15 C -0.0291(4) 0.70341(7) 0.4100(3) 0.0312 1.0000 Uani . . . . . .
C16 C 0.0116(4) 0.67154(7) 0.3296(3) 0.0281 1.0000 Uani . . . . . .
O17 O -0.2378(3) 0.75484(5) 0.4623(2) 0.0379 1.0000 Uani . . . . . .
C18 C -0.4285(5) 0.77603(9) 0.4296(4) 0.0491 1.0000 Uani . . . . . .
C19 C 0.1887(4) 0.59032(6) 0.2695(3) 0.0236 1.0000 Uani . . . . . .
C20 C 0.0452(4) 0.56857(7) 0.3436(3) 0.0264 1.0000 Uani . . . . . .
C21 C 0.1142(4) 0.54817(7) 0.4736(3) 0.0268 1.0000 Uani . . . . . .
C22 C 0.3299(4) 0.54891(6) 0.5302(3) 0.0244 1.0000 Uani . . . . . .
C23 C 0.4745(4) 0.57008(7) 0.4551(3) 0.0262 1.0000 Uani . . . . . .
C24 C 0.4048(4) 0.59077(7) 0.3256(3) 0.0270 1.0000 Uani . . . . . .
C25 C 0.3980(4) 0.52762(7) 0.6726(3) 0.0264 1.0000 Uani . . . . . .
O26 O 0.2781(3) 0.51118(6) 0.7505(2) 0.0400 1.0000 Uani . . . . . .
O27 O 0.6125(3) 0.52890(5) 0.7051(2) 0.0312 1.0000 Uani . . . . . .
C28 C 0.6955(4) 0.50887(8) 0.8408(3) 0.0360 1.0000 Uani . . . . . .
H11 H 0.2219 0.6328 0.1151 0.0280 1.0000 Uiso R . . . . .
H22 H 0.2670 0.5731 -0.0044 0.0341 1.0000 Uiso R . . . . .
H21 H 0.0115 0.5694 -0.0205 0.0341 1.0000 Uiso R . . . . .
H41 H -0.0344 0.6204 -0.3690 0.0399 1.0000 Uiso R . . . . .
H42 H -0.1674 0.5942 -0.2561 0.0405 1.0000 Uiso R . . . . .
H81 H 0.4762 0.6725 -0.4807 0.0418 1.0000 Uiso R . . . . .
H82 H 0.6232 0.6489 -0.3574 0.0427 1.0000 Uiso R . . . . .
H92 H 0.6793 0.7124 -0.3170 0.0922 1.0000 Uiso R . . . . .
H91 H 0.4305 0.7168 -0.2902 0.0939 1.0000 Uiso R . . . . .
H93 H 0.5840 0.6943 -0.1732 0.0929 1.0000 Uiso R . . . . .
H121 H -0.4231 0.6712 0.0977 0.0312 1.0000 Uiso R . . . . .
H131 H -0.4904 0.7249 0.2297 0.0349 1.0000 Uiso R . . . . .
H151 H 0.0687 0.7115 0.4899 0.0382 1.0000 Uiso R . . . . .
H161 H 0.1403 0.6583 0.3549 0.0339 1.0000 Uiso R . . . . .
H181 H -0.4253 0.7963 0.5025 0.0736 1.0000 Uiso R . . . . .
H183 H -0.4326 0.7855 0.3236 0.0735 1.0000 Uiso R . . . . .
H182 H -0.5537 0.7604 0.4422 0.0736 1.0000 Uiso R . . . . .
H201 H -0.1003 0.5675 0.3048 0.0323 1.0000 Uiso R . . . . .
H211 H 0.0154 0.5338 0.5245 0.0320 1.0000 Uiso R . . . . .
H231 H 0.6211 0.5708 0.4916 0.0306 1.0000 Uiso R . . . . .
H241 H 0.5044 0.6050 0.2751 0.0321 1.0000 Uiso R . . . . .
H283 H 0.8505 0.5087 0.8404 0.0537 1.0000 Uiso R . . . . .
H282 H 0.6529 0.5209 0.9332 0.0534 1.0000 Uiso R . . . . .
H281 H 0.6419 0.4836 0.8355 0.0535 1.0000 Uiso R . . . . .
H101 H -0.1753 0.6254 0.0397 0.0301 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.21(9)
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
C1 . C2 . 1.543(3) yes
C1 . N10 . 1.453(3) yes
C1 . C19 . 1.522(3) yes
C1 . H11 . 0.997 no
C2 . C3 . 1.500(3) yes
C2 . H22 . 0.984 no
C2 . H21 . 0.980 no
C3 . C4 . 1.327(3) yes
C3 . C5 . 1.488(3) yes
C4 . H41 . 0.956 no
C4 . H42 . 0.945 no
C5 . O6 . 1.212(3) yes
C5 . O7 . 1.339(3) yes
O7 . C8 . 1.453(3) yes
C8 . C9 . 1.482(4) yes
C8 . H81 . 0.984 no
C8 . H82 . 0.981 no
C9 . H92 . 0.971 no
C9 . H91 . 0.975 no
C9 . H93 . 0.961 no
N10 . C11 . 1.398(3) yes
N10 . H101 . 0.864 no
C11 . C12 . 1.397(3) yes
C11 . C16 . 1.400(3) yes
C12 . C13 . 1.387(3) yes
C12 . H121 . 0.942 no
C13 . C14 . 1.389(3) yes
C13 . H131 . 0.949 no
C14 . C15 . 1.389(3) yes
C14 . O17 . 1.380(3) yes
C15 . C16 . 1.385(3) yes
C15 . H151 . 0.933 no
C16 . H161 . 0.946 no
O17 . C18 . 1.426(3) yes
C18 . H181 . 0.969 no
C18 . H183 . 0.980 no
C18 . H182 . 0.979 no
C19 . C20 . 1.389(3) yes
C19 . C24 . 1.396(3) yes
C20 . C21 . 1.388(3) yes
C20 . H201 . 0.944 no
C21 . C22 . 1.395(3) yes
C21 . H211 . 0.943 no
C22 . C23 . 1.386(3) yes
C22 . C25 . 1.489(3) yes
C23 . C24 . 1.391(3) yes
C23 . H231 . 0.944 no
C24 . H241 . 0.943 no
C25 . O26 . 1.205(3) yes
C25 . O27 . 1.346(3) yes
O27 . C28 . 1.443(3) yes
C28 . H283 . 0.967 no
C28 . H282 . 0.969 no
C28 . H281 . 0.975 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 . C1 . N10 . 109.70(19) yes
C2 . C1 . C19 . 108.86(19) yes
N10 . C1 . C19 . 112.61(18) yes
C2 . C1 . H11 . 108.1 no
N10 . C1 . H11 . 109.2 no
C19 . C1 . H11 . 108.3 no
C1 . C2 . C3 . 113.5(2) yes
C1 . C2 . H22 . 107.7 no
C3 . C2 . H22 . 108.7 no
C1 . C2 . H21 . 108.3 no
C3 . C2 . H21 . 109.9 no
H22 . C2 . H21 . 108.6 no
C2 . C3 . C4 . 123.9(2) yes
C2 . C3 . C5 . 115.6(2) yes
C4 . C3 . C5 . 120.4(2) yes
C3 . C4 . H41 . 120.4 no
C3 . C4 . H42 . 120.6 no
H41 . C4 . H42 . 119.0 no
C3 . C5 . O6 . 123.0(2) yes
C3 . C5 . O7 . 113.6(2) yes
O6 . C5 . O7 . 123.4(2) yes
C5 . O7 . C8 . 117.1(2) yes
O7 . C8 . C9 . 111.6(2) yes
O7 . C8 . H81 . 107.1 no
C9 . C8 . H81 . 109.1 no
O7 . C8 . H82 . 109.8 no
C9 . C8 . H82 . 110.1 no
H81 . C8 . H82 . 109.1 no
C8 . C9 . H92 . 110.8 no
C8 . C9 . H91 . 109.5 no
H92 . C9 . H91 . 110.2 no
C8 . C9 . H93 . 109.6 no
H92 . C9 . H93 . 108.5 no
H91 . C9 . H93 . 108.2 no
C1 . N10 . C11 . 120.22(19) yes
C1 . N10 . H101 . 114.8 no
C11 . N10 . H101 . 113.6 no
N10 . C11 . C12 . 120.3(2) yes
N10 . C11 . C16 . 122.2(2) yes
C12 . C11 . C16 . 117.5(2) yes
C11 . C12 . C13 . 121.9(2) yes
C11 . C12 . H121 . 119.0 no
C13 . C12 . H121 . 119.1 no
C12 . C13 . C14 . 119.8(2) yes
C12 . C13 . H131 . 119.7 no
C14 . C13 . H131 . 120.5 no
C13 . C14 . C15 . 119.1(2) yes
C13 . C14 . O17 . 125.4(2) yes
C15 . C14 . O17 . 115.5(2) yes
C14 . C15 . C16 . 120.9(2) yes
C14 . C15 . H151 . 119.1 no
C16 . C15 . H151 . 120.0 no
C11 . C16 . C15 . 120.8(2) yes
C11 . C16 . H161 . 119.5 no
C15 . C16 . H161 . 119.6 no
C14 . O17 . C18 . 116.9(2) yes
O17 . C18 . H181 . 107.9 no
O17 . C18 . H183 . 109.5 no
H181 . C18 . H183 . 110.1 no
O17 . C18 . H182 . 109.0 no
H181 . C18 . H182 . 110.0 no
H183 . C18 . H182 . 110.3 no
C1 . C19 . C20 . 121.7(2) yes
C1 . C19 . C24 . 119.1(2) yes
C20 . C19 . C24 . 119.0(2) yes
C19 . C20 . C21 . 120.6(2) yes
C19 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 119.6 no
C20 . C21 . C22 . 120.2(2) yes
C20 . C21 . H211 . 120.2 no
C22 . C21 . H211 . 119.6 no
C21 . C22 . C23 . 119.4(2) yes
C21 . C22 . C25 . 119.0(2) yes
C23 . C22 . C25 . 121.6(2) yes
C22 . C23 . C24 . 120.4(2) yes
C22 . C23 . H231 . 120.5 no
C24 . C23 . H231 . 119.1 no
C19 . C24 . C23 . 120.3(2) yes
C19 . C24 . H241 . 119.9 no
C23 . C24 . H241 . 119.8 no
C22 . C25 . O26 . 125.0(2) yes
C22 . C25 . O27 . 111.6(2) yes
O26 . C25 . O27 . 123.4(2) yes
C25 . O27 . C28 . 116.0(2) yes
O27 . C28 . H283 . 107.1 no
O27 . C28 . H282 . 110.0 no
H283 . C28 . H282 . 110.3 no
O27 . C28 . H281 . 109.6 no
H283 . C28 . H281 . 109.5 no
H282 . C28 . H281 . 110.4 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
C9 . H92 . O17 1_654 137 0.97 2.54 3.321(4) yes
N10 . H101 . O6 1_455 156 0.86 2.39 3.202(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
5 1 3 x .
-2 0 10 x .
-4 1 7 x .
